# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
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data_mo_2016160_0m
_database_code_depnum_ccdc_archive 'CCDC 1506811'
_audit_update_record
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date 2017-07-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C3 H N9 O10, 2(H2 O)'
_chemical_formula_sum 'C3 H5 N9 O12'
_chemical_formula_weight 359.16
_chemical_absolute_configuration ?
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 7.4840(4)
_cell_length_b 7.8907(4)
_cell_length_c 10.2465(5)
_cell_angle_alpha 90
_cell_angle_beta 93.122(3)
_cell_angle_gamma 90
_cell_volume 604.20(5)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4367
_cell_measurement_temperature 296
_cell_measurement_theta_max 27.461
_cell_measurement_theta_min 2.725
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.200
_exptl_absorpt_correction_T_max 0.957
_exptl_absorpt_correction_T_min 0.946
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0431 before and 0.0326 after correction. The Ratio of minimum to maximum transmission is 0.9359. The \l/2 correction factor is 0.0015.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear whiteish colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier whiteish
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.974
_exptl_crystal_density_meas .
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 364
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.22
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0490
_diffrn_reflns_av_unetI/netI 0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 5452
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 26.000
_diffrn_reflns_theta_max 27.465
_diffrn_reflns_theta_min 1.990
_diffrn_ambient_temperature 296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.868
_reflns_Friedel_fraction_full 1.000
_reflns_Friedel_fraction_max 1.000
_reflns_number_gt 2549
_reflns_number_total 2641
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection ?
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max 0.355
_refine_diff_density_min -0.464
_refine_diff_density_rms 0.085
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack -2(2)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.261
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 224
_refine_ls_number_reflns 2641
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0379
_refine_ls_R_factor_gt 0.0314
_refine_ls_restrained_S_all 1.266
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0732P)^2^+0.2583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0867
_refine_ls_wR_factor_ref 0.1263
_refine_special_details
;
Refined as a 2-component inversion twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 3(2)
-2(2)
2. Fixed Uiso
At 1.2 times of:
All N(H) groups
At 1.5 times of:
All O(H,H) groups
3. Restrained distances
H2WA-H2WB
1.46 with sigma of 0.02
H1WB-H1WA
1.46 with sigma of 0.02
4.a Free rotating group:
O2W(H2WA,H2WB), O1W(H1WA,H1WB)
4.b Aromatic/amide H refined with riding coordinates:
N4(H4)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
_atom_sites_special_details
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual = -1, Ralpha = 0.048
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.8689(4) 3.1580(4) 2.9608(3) 0.0220(6) Uani 1 1 d . . . . .
O2W O 0.5742(4) 3.4277(3) 2.9129(3) 0.0194(5) Uani 1 1 d . . . . .
H2WA H 0.5413 3.3252 2.9200 0.029 Uiso 1 1 d DG . . . .
H2WB H 0.6830 3.4307 2.8932 0.029 Uiso 1 1 d DG . . . .
O2 O 0.7321(4) 3.9453(3) 2.7412(3) 0.0203(6) Uani 1 1 d . . . . .
O1 O 0.7361(4) 3.7504(4) 2.8916(3) 0.0207(6) Uani 1 1 d . . . . .
O3 O 1.1035(4) 3.0546(3) 2.8703(3) 0.0201(6) Uani 1 1 d . . . . .
O1W O 0.4868(4) 3.1087(3) 2.8789(3) 0.0198(6) Uani 1 1 d . . . . .
H1WA H 0.5637 3.0443 2.8462 0.030 Uiso 1 1 d DG . . . .
H1WB H 0.3888 3.1030 2.8331 0.030 Uiso 1 1 d DG . . . .
O6 O 1.3084(4) 3.9004(4) 2.6386(3) 0.0245(6) Uani 1 1 d . . . . .
O8 O 1.2315(5) 3.7271(4) 2.4212(3) 0.0274(7) Uani 1 1 d . . . . .
O10 O 1.5427(4) 3.5615(4) 2.6353(3) 0.0263(6) Uani 1 1 d . . . . .
O9 O 1.3658(4) 3.3737(4) 2.5385(3) 0.0269(6) Uani 1 1 d . . . . .
O5 O 1.3328(4) 3.7486(4) 2.8163(3) 0.0241(6) Uani 1 1 d . . . . .
O7 O 0.9943(4) 3.5896(5) 2.4699(3) 0.0296(7) Uani 1 1 d . . . . .
N6 N 0.9961(4) 3.1672(4) 2.8901(3) 0.0152(6) Uani 1 1 d . . . . .
N1 N 0.8958(4) 3.4551(4) 2.8317(3) 0.0140(6) Uani 1 1 d . . . . .
N7 N 1.2966(4) 3.7711(4) 2.7000(3) 0.0158(6) Uani 1 1 d . . . . .
N5 N 0.7897(4) 3.8083(4) 2.7889(3) 0.0149(6) Uani 1 1 d . . . . .
N3 N 1.1204(4) 3.5144(4) 2.7094(3) 0.0153(6) Uani 1 1 d . . . . .
N8 N 1.1419(4) 3.6463(4) 2.4923(3) 0.0180(6) Uani 1 1 d . . . . .
N2 N 1.1572(4) 3.3537(4) 2.7544(3) 0.0147(6) Uani 1 1 d . . . . .
N4 N 0.9170(4) 3.7339(4) 2.7218(3) 0.0167(6) Uani 1 1 d . . . . .
H4 H 0.9658 3.7844 2.6585 0.020 Uiso 1 1 calc R . . . .
N9 N 1.3987(4) 3.5018(4) 2.5988(3) 0.0169(6) Uani 1 1 d . . . . .
C2 C 0.9640(5) 3.5768(4) 2.7588(3) 0.0140(6) Uani 1 1 d . . . . .
C1 C 1.0190(5) 3.3288(4) 2.8237(3) 0.0127(6) Uani 1 1 d . . . . .
C3 C 1.2323(5) 3.6060(4) 2.6291(3) 0.0139(6) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0164(13) 0.0250(14) 0.0250(13) 0.0067(11) 0.0066(10) 0.0000(11)
O2W 0.0158(12) 0.0140(12) 0.0290(13) 0.0029(10) 0.0056(10) -0.0005(10)
O2 0.0223(14) 0.0153(12) 0.0238(13) 0.0048(10) 0.0048(10) 0.0079(10)
O1 0.0216(14) 0.0200(13) 0.0215(12) 0.0030(10) 0.0101(11) 0.0027(10)
O3 0.0179(13) 0.0147(12) 0.0277(13) 0.0013(11) 0.0022(10) 0.0029(10)
O1W 0.0135(12) 0.0187(13) 0.0276(13) -0.0025(10) 0.0035(10) 0.0008(10)
O6 0.0274(15) 0.0182(14) 0.0280(13) 0.0018(11) 0.0025(11) -0.0053(11)
O8 0.0356(17) 0.0285(16) 0.0185(12) 0.0037(12) 0.0041(12) -0.0034(13)
O10 0.0106(12) 0.0351(17) 0.0334(14) -0.0063(13) 0.0026(10) -0.0003(12)
O9 0.0269(15) 0.0246(15) 0.0299(14) -0.0057(12) 0.0087(12) 0.0031(12)
O5 0.0259(15) 0.0281(14) 0.0179(12) -0.0023(11) -0.0011(11) -0.0016(12)
O7 0.0176(13) 0.0468(19) 0.0238(14) -0.0078(13) -0.0041(11) -0.0038(13)
N6 0.0137(14) 0.0155(14) 0.0161(13) -0.0007(11) 0.0000(11) 0.0009(12)
N1 0.0120(13) 0.0137(14) 0.0162(13) -0.0005(10) 0.0014(10) 0.0017(11)
N7 0.0131(14) 0.0150(15) 0.0195(13) -0.0037(11) 0.0024(11) -0.0002(11)
N5 0.0123(13) 0.0139(13) 0.0185(13) -0.0008(11) 0.0000(11) -0.0001(11)
N3 0.0122(14) 0.0169(14) 0.0171(13) 0.0006(11) 0.0035(11) 0.0012(12)
N8 0.0215(16) 0.0182(15) 0.0140(13) -0.0006(11) -0.0006(12) 0.0030(12)
N2 0.0122(14) 0.0158(14) 0.0161(12) -0.0015(11) 0.0022(11) 0.0002(11)
N4 0.0156(15) 0.0149(14) 0.0203(13) 0.0031(11) 0.0066(11) 0.0014(12)
N9 0.0157(15) 0.0190(15) 0.0166(13) 0.0019(11) 0.0059(11) 0.0025(12)
C2 0.0116(15) 0.0157(16) 0.0148(14) -0.0036(13) 0.0022(11) -0.0004(12)
C1 0.0116(15) 0.0114(15) 0.0150(13) -0.0017(11) 0.0006(12) 0.0006(12)
C3 0.0121(15) 0.0143(15) 0.0152(14) -0.0002(12) 0.0006(11) 0.0011(13)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 N6 1.230(4) . ?
O2W H2WA 0.8499 . ?
O2W H2WB 0.8501 . ?
O2 N5 1.254(4) . ?
O1 N5 1.234(4) . ?
O3 N6 1.222(4) . ?
O1W H1WA 0.8502 . ?
O1W H1WB 0.8502 . ?
O6 N7 1.204(4) . ?
O8 N8 1.201(4) . ?
O10 N9 1.217(5) . ?
O9 N9 1.203(4) . ?
O5 N7 1.220(4) . ?
O7 N8 1.203(5) . ?
N6 C1 1.460(4) . ?
N1 C2 1.335(5) . ?
N1 C1 1.364(4) . ?
N7 C3 1.555(4) . ?
N5 N4 1.340(5) . ?
N3 N2 1.373(4) . ?
N3 C2 1.391(4) . ?
N3 C3 1.406(5) . ?
N8 C3 1.556(4) . ?
N2 C1 1.301(5) . ?
N4 H4 0.8600 . ?
N4 C2 1.337(5) . ?
N9 C3 1.538(4) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H2WA O2W H2WB 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?
O4 N6 C1 116.1(3) . . ?
O3 N6 O4 126.3(3) . . ?
O3 N6 C1 117.6(3) . . ?
C2 N1 C1 102.2(3) . . ?
O6 N7 O5 128.0(3) . . ?
O6 N7 C3 119.7(3) . . ?
O5 N7 C3 112.3(3) . . ?
O2 N5 N4 114.6(3) . . ?
O1 N5 O2 122.1(3) . . ?
O1 N5 N4 123.3(3) . . ?
N2 N3 C2 111.3(3) . . ?
N2 N3 C3 123.8(3) . . ?
C2 N3 C3 124.8(3) . . ?
O8 N8 O7 128.3(3) . . ?
O8 N8 C3 115.2(3) . . ?
O7 N8 C3 116.5(3) . . ?
C1 N2 N3 99.9(3) . . ?
N5 N4 H4 121.8 . . ?
C2 N4 N5 116.3(3) . . ?
C2 N4 H4 121.8 . . ?
O10 N9 C3 116.4(3) . . ?
O9 N9 O10 129.5(3) . . ?
O9 N9 C3 114.1(3) . . ?
N1 C2 N3 107.7(3) . . ?
N1 C2 N4 136.3(3) . . ?
N4 C2 N3 116.0(3) . . ?
N1 C1 N6 120.9(3) . . ?
N2 C1 N6 120.2(3) . . ?
N2 C1 N1 118.9(3) . . ?
N7 C3 N8 111.0(3) . . ?
N3 C3 N7 109.7(3) . . ?
N3 C3 N8 112.8(3) . . ?
N3 C3 N9 111.0(3) . . ?
N9 C3 N7 108.0(3) . . ?
N9 C3 N8 104.1(3) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 N6 C1 N1 -5.6(5) . . . . ?
O4 N6 C1 N2 175.1(3) . . . . ?
O2 N5 N4 C2 -170.9(3) . . . . ?
O1 N5 N4 C2 11.1(5) . . . . ?
O3 N6 C1 N1 174.2(3) . . . . ?
O3 N6 C1 N2 -5.1(5) . . . . ?
O6 N7 C3 N3 -141.2(3) . . . . ?
O6 N7 C3 N8 -15.8(5) . . . . ?
O6 N7 C3 N9 97.7(4) . . . . ?
O8 N8 C3 N7 55.2(4) . . . . ?
O8 N8 C3 N3 178.7(3) . . . . ?
O8 N8 C3 N9 -60.8(4) . . . . ?
O10 N9 C3 N7 1.2(4) . . . . ?
O10 N9 C3 N3 -119.1(3) . . . . ?
O10 N9 C3 N8 119.2(3) . . . . ?
O9 N9 C3 N7 -176.9(3) . . . . ?
O9 N9 C3 N3 62.8(4) . . . . ?
O9 N9 C3 N8 -58.9(4) . . . . ?
O5 N7 C3 N3 40.1(4) . . . . ?
O5 N7 C3 N8 165.4(3) . . . . ?
O5 N7 C3 N9 -81.0(3) . . . . ?
O7 N8 C3 N7 -126.7(3) . . . . ?
O7 N8 C3 N3 -3.1(5) . . . . ?
O7 N8 C3 N9 117.3(3) . . . . ?
N5 N4 C2 N1 15.6(6) . . . . ?
N5 N4 C2 N3 -166.5(3) . . . . ?
N3 N2 C1 N6 178.3(3) . . . . ?
N3 N2 C1 N1 -1.1(4) . . . . ?
N2 N3 C2 N1 -2.2(4) . . . . ?
N2 N3 C2 N4 179.3(3) . . . . ?
N2 N3 C3 N7 -118.9(3) . . . . ?
N2 N3 C3 N8 116.8(3) . . . . ?
N2 N3 C3 N9 0.4(4) . . . . ?
C2 N1 C1 N6 -179.6(3) . . . . ?
C2 N1 C1 N2 -0.2(4) . . . . ?
C2 N3 N2 C1 1.9(3) . . . . ?
C2 N3 C3 N7 57.6(4) . . . . ?
C2 N3 C3 N8 -66.6(4) . . . . ?
C2 N3 C3 N9 176.9(3) . . . . ?
C1 N1 C2 N3 1.4(4) . . . . ?
C1 N1 C2 N4 179.5(4) . . . . ?
C3 N3 N2 C1 178.9(3) . . . . ?
C3 N3 C2 N1 -179.1(3) . . . . ?
C3 N3 C2 N4 2.4(5) . . . . ?
_iucr_refine_instructions_details
;
mo_2016160_0m.res created by SHELXL-2014/7
TITL mo_2016160_0m_a.res in P2(1)
REM Old TITL mo_2016160_0m in P21 #4
REM SHELXT solution in P2(1)
REM R1 0.091, Rweak 0.025, Alpha 0.017, Orientation as input
REM Flack x = 0.247 ( 0.286 ) from Parsons' quotients
REM Formula found by SHELXT: C15 N4 O5
CELL 0.71073 7.484 7.8907 10.2465 90 93.122 90
ZERR 2 0.0004 0.0004 0.0005 0 0.003 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 6 10 18 24
DFIX 1.46 H2Wa H2Wb
DFIX 1.46 H1Wb H1Wa
L.S. 20
PLAN 20
TEMP 22.85
BOND $H
LIST 6
CONF
fmap 2
acta 52
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM
REM
REM
WGHT 0.073200 0.258300
BASF -1.70999
FVAR 1.26244
O4 4 0.868893 3.158041 2.960796 11.00000 0.01642 0.02503 =
0.02503 0.00666 0.00657 0.00004
AFIX 6
O2W 4 0.574208 3.427701 2.912907 11.00000 0.01583 0.01398 =
0.02898 0.00290 0.00561 -0.00047
H2WA 2 0.541253 3.325200 2.920022 11.00000 -1.50000
H2WB 2 0.683040 3.430733 2.893211 11.00000 -1.50000
AFIX 0
O2 4 0.732150 3.945336 2.741164 11.00000 0.02231 0.01527 =
0.02382 0.00481 0.00480 0.00788
O1 4 0.736092 3.750439 2.891648 11.00000 0.02161 0.01997 =
0.02146 0.00301 0.01007 0.00270
O3 4 1.103525 3.054571 2.870306 11.00000 0.01787 0.01472 =
0.02772 0.00132 0.00223 0.00293
AFIX 6
O1W 4 0.486778 3.108658 2.878891 11.00000 0.01345 0.01868 =
0.02763 -0.00251 0.00346 0.00078
H1WA 2 0.563741 3.044331 2.846181 11.00000 -1.50000
H1WB 2 0.388781 3.102998 2.833068 11.00000 -1.50000
AFIX 0
O6 4 1.308413 3.900406 2.638594 11.00000 0.02743 0.01818 =
0.02798 0.00179 0.00252 -0.00534
O8 4 1.231517 3.727133 2.421159 11.00000 0.03562 0.02850 =
0.01848 0.00366 0.00410 -0.00335
O10 4 1.542722 3.561471 2.635347 11.00000 0.01061 0.03510 =
0.03339 -0.00626 0.00261 -0.00030
O9 4 1.365781 3.373661 2.538516 11.00000 0.02695 0.02464 =
0.02986 -0.00569 0.00867 0.00310
O5 4 1.332799 3.748611 2.816253 11.00000 0.02591 0.02811 =
0.01794 -0.00235 -0.00112 -0.00164
O7 4 0.994281 3.589551 2.469889 11.00000 0.01763 0.04683 =
0.02383 -0.00776 -0.00413 -0.00383
N6 3 0.996141 3.167164 2.890052 11.00000 0.01374 0.01552 =
0.01612 -0.00065 0.00004 0.00090
N1 3 0.895750 3.455119 2.831732 11.00000 0.01204 0.01366 =
0.01623 -0.00052 0.00137 0.00173
N7 3 1.296648 3.771147 2.700019 11.00000 0.01311 0.01502 =
0.01947 -0.00371 0.00243 -0.00018
N5 3 0.789742 3.808277 2.788941 11.00000 0.01228 0.01395 =
0.01847 -0.00085 0.00001 -0.00011
N3 3 1.120382 3.514384 2.709386 11.00000 0.01224 0.01693 =
0.01705 0.00060 0.00348 0.00119
N8 3 1.141899 3.646280 2.492344 11.00000 0.02154 0.01820 =
0.01403 -0.00062 -0.00061 0.00296
N2 3 1.157243 3.353657 2.754446 11.00000 0.01224 0.01582 =
0.01610 -0.00152 0.00220 0.00024
N4 3 0.917015 3.733865 2.721818 11.00000 0.01560 0.01494 =
0.02027 0.00307 0.00657 0.00135
AFIX 43
H4 2 0.965819 3.784366 2.658452 11.00000 -1.20000
AFIX 0
N9 3 1.398684 3.501786 2.598797 11.00000 0.01569 0.01902 =
0.01657 0.00194 0.00586 0.00246
C2 1 0.963957 3.576813 2.758766 11.00000 0.01158 0.01566 =
0.01483 -0.00358 0.00222 -0.00037
C1 1 1.018967 3.328750 2.823654 11.00000 0.01159 0.01141 =
0.01502 -0.00169 0.00061 0.00065
C3 1 1.232347 3.605983 2.629139 11.00000 0.01213 0.01432 =
0.01525 -0.00020 0.00058 0.00110
HKLF 4
REM mo_2016160_0m_a.res in P2(1)
REM R1 = 0.0314 for 2549 Fo > 4sig(Fo) and 0.0379 for all 2641 data
REM 224 parameters refined using 3 restraints
END
WGHT 0.0732 0.2583
REM Highest difference peak 0.355, deepest hole -0.464, 1-sigma level 0.085
Q1 1 0.5469 3.4768 2.9979 11.00000 0.05 0.35
Q2 1 1.4410 3.7417 2.4345 11.00000 0.05 0.29
Q3 1 0.4698 3.1511 2.7120 11.00000 0.05 0.28
Q4 1 1.4494 3.5467 2.4306 11.00000 0.05 0.27
Q5 1 0.8766 3.9369 2.5738 11.00000 0.05 0.27
Q6 1 1.4746 3.3406 2.4372 11.00000 0.05 0.26
Q7 1 0.5527 3.0629 2.8108 11.00000 0.05 0.26
Q8 1 0.9150 3.7481 2.5642 11.00000 0.05 0.26
Q9 1 1.1232 3.7471 2.3180 11.00000 0.05 0.25
Q10 1 0.9049 3.1439 2.7963 11.00000 0.05 0.25
Q11 1 0.9486 3.3648 2.8104 11.00000 0.05 0.23
Q12 1 0.3082 3.1016 2.7528 11.00000 0.05 0.23
Q13 1 0.5306 2.8683 2.8375 11.00000 0.05 0.23
Q14 1 1.0934 3.3433 2.8005 11.00000 0.05 0.22
Q15 1 1.4458 3.6566 2.5500 11.00000 0.05 0.22
Q16 1 1.4927 3.9501 2.7041 11.00000 0.05 0.22
Q17 1 1.1376 3.3483 2.5557 11.00000 0.05 0.22
Q18 1 1.4028 3.8432 2.5666 11.00000 0.05 0.22
Q19 1 1.3054 3.7390 2.4293 11.00000 0.05 0.22
Q20 1 1.2486 3.3128 2.7714 11.00000 0.05 0.21
REM The information below was added by Olex2.
REM
REM R1 = 0.0314 for 2549 Fo > 4sig(Fo) and 0.0379 for all 5464 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.35, deepest hole -0.46
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0379
REM R1_gt = 0.0314
REM wR_ref = 0.1263
REM GOOF = 1.261
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 5464
REM Reflections_gt = 2549
REM Parameters = n/a
REM Hole = -0.46
REM Peak = 0.35
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 3(2)
2 -2(2)
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_a
_database_code_depnum_ccdc_archive 'CCDC 1502833'
_audit_update_record
;
2016-09-06 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date 2016-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C3 N9 O10, C2 H5 N4'
_chemical_formula_sum 'C5 H5 N13 O10'
_chemical_formula_weight 407.22
_chemical_absolute_configuration ?
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 29
_space_group_name_H-M_alt 'P c a 21'
_space_group_name_Hall 'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
_cell_length_a 23.003(2)
_cell_length_b 6.7490(7)
_cell_length_c 19.422(2)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 3015.1(6)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 3572
_cell_measurement_temperature 296.15
_cell_measurement_theta_max 20.377
_cell_measurement_theta_min 2.745
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.170
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.6181
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0748 before and 0.0569 after correction.
The Ratio of minimum to maximum transmission is 0.8290.
The \l/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear whiteish colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier whiteish
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.794
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1648
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.2
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0483
_diffrn_reflns_av_unetI/netI 0.0594
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 22518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.370
_diffrn_reflns_theta_min 1.771
_diffrn_ambient_temperature 296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.939
_reflns_Friedel_fraction_full 1.000
_reflns_Friedel_fraction_max 1.000
_reflns_number_gt 3165
_reflns_number_total 5696
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection ?
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.468
_refine_diff_density_min -0.244
_refine_diff_density_rms 0.052
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack 0(3)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.006
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 512
_refine_ls_number_reflns 5696
_refine_ls_number_restraints 166
_refine_ls_R_factor_all 0.1222
_refine_ls_R_factor_gt 0.0602
_refine_ls_restrained_S_all 0.999
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0972P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1454
_refine_ls_wR_factor_ref 0.1774
_refine_special_details
;
Refined as a 2-component inversion twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 1(3) 0(3)
2. Fixed Uiso
At 1.2 times of:
All C(H) groups, All N(H) groups, All N(H,H) groups
3. Restrained distances
O2-N4
2.9 with sigma of 0.02
O12-N17
2.9 with sigma of 0.02
N17-H17
0.88 with sigma of 0.02
4. Restrained planarity
C6, C7, N15, N16, N17
with sigma of 0.1
5. Rigid bond restraints
All non-hydrogen atoms
with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Uiso/Uaniso restraints and constraints
Uanis(O16) \\sim Ueq, Uanis(O15) \\sim Ueq, Uanis(N25) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
7.a Rotating group:
N14(H14A,H14B), N1(H1A,H1B)
7.b Aromatic/amide H refined with riding coordinates:
C6(H6), C7(H7), C1(H1), C2(H2), N4(H4)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C -0.3346(3) -0.6836(9) -0.3949(4) 0.0459(15) Uani 1 1 d . U . . .
C4 C -0.4066(3) -0.8443(9) -0.3624(4) 0.0476(15) Uani 1 1 d . U . . .
C5 C -0.3883(3) -0.5039(10) -0.4876(4) 0.0484(16) Uani 1 1 d . U . . .
N5 N -0.2387(3) -0.6228(9) -0.3790(4) 0.0610(17) Uani 1 1 d . U . . .
N6 N -0.2868(2) -0.5852(8) -0.4135(4) 0.0590(17) Uani 1 1 d . U . . .
N7 N -0.3501(2) -0.8194(8) -0.3488(3) 0.0503(14) Uani 1 1 d . U . . .
N8 N -0.4416(3) -0.9829(9) -0.3220(4) 0.0600(16) Uani 1 1 d . U . . .
N9 N -0.4311(2) -0.7468(8) -0.4114(3) 0.0507(14) Uani 1 1 d . U . . .
N10 N -0.3840(2) -0.6391(8) -0.4333(3) 0.0487(14) Uani 1 1 d . U . . .
N11 N -0.3561(3) -0.5775(13) -0.5524(4) 0.0733(19) Uani 1 1 d . U . . .
N12 N -0.3661(3) -0.2969(11) -0.4658(5) 0.076(2) Uani 1 1 d . U . . .
N13 N -0.4522(3) -0.4781(11) -0.5088(4) 0.0659(17) Uani 1 1 d . U . . .
O1 O -0.2352(2) -0.7431(9) -0.3315(3) 0.0816(17) Uani 1 1 d . U . . .
O2 O -0.1950(2) -0.5238(9) -0.3963(4) 0.0855(19) Uani 1 1 d D U . . .
O3 O -0.4182(3) -1.0709(9) -0.2761(3) 0.0765(16) Uani 1 1 d . U . . .
O4 O -0.4927(3) -1.0016(11) -0.3368(4) 0.104(2) Uani 1 1 d . U . . .
O5 O -0.3343(3) -0.7382(9) -0.5482(3) 0.0850(18) Uani 1 1 d . U . . .
O6 O -0.3593(4) -0.4750(14) -0.6019(5) 0.140(4) Uani 1 1 d . U . . .
O7 O -0.3509(4) -0.1904(12) -0.5111(5) 0.136(3) Uani 1 1 d . U . . .
O8 O -0.3695(4) -0.2640(10) -0.4057(5) 0.115(3) Uani 1 1 d . U . . .
O9 O -0.4697(3) -0.5777(15) -0.5540(5) 0.119(3) Uani 1 1 d . U . . .
O10 O -0.4791(3) -0.3617(10) -0.4739(4) 0.106(2) Uani 1 1 d . U . . .
C8 C -0.5852(3) -0.1245(10) -0.6065(4) 0.0485(16) Uani 1 1 d . U . . .
C9 C -0.6574(3) -0.2824(9) -0.6406(4) 0.0477(16) Uani 1 1 d . U . . .
C10 C -0.6378(3) 0.0677(10) -0.5186(4) 0.0528(17) Uani 1 1 d . U . . .
N18 N -0.4871(3) -0.0855(10) -0.6183(4) 0.0612(16) Uani 1 1 d . U . . .
N19 N -0.5358(3) -0.0328(9) -0.5871(3) 0.0619(17) Uani 1 1 d . U . . .
N20 N -0.5998(2) -0.2620(7) -0.6516(3) 0.0514(14) Uani 1 1 d . U . . .
N21 N -0.6922(3) -0.4210(9) -0.6815(4) 0.0606(16) Uani 1 1 d . U . . .
N22 N -0.6820(2) -0.1748(8) -0.5933(3) 0.0504(13) Uani 1 1 d . U . . .
N23 N -0.6343(2) -0.0654(8) -0.5712(3) 0.0508(14) Uani 1 1 d . U . . .
N24 N -0.6127(3) -0.0156(14) -0.4510(4) 0.089(2) Uani 1 1 d . U . . .
N25 N -0.6092(4) 0.2665(12) -0.5372(7) 0.097(3) Uani 1 1 d . U . . .
N26 N -0.7030(3) 0.1151(11) -0.5034(4) 0.0672(17) Uani 1 1 d . U . . .
O11 O -0.4854(2) -0.2112(11) -0.6636(4) 0.103(2) Uani 1 1 d . U . . .
O12 O -0.4431(2) -0.0004(10) -0.6004(4) 0.097(2) Uani 1 1 d D U . . .
O13 O -0.6661(3) -0.5163(8) -0.7249(3) 0.0792(17) Uani 1 1 d . U . . .
O14 O -0.7428(3) -0.4334(10) -0.6689(4) 0.099(2) Uani 1 1 d . U . . .
O15 O -0.6102(4) 0.3105(12) -0.5943(7) 0.147(4) Uani 1 1 d . U . . .
O16 O -0.5875(5) 0.3508(17) -0.4884(7) 0.216(7) Uani 1 1 d . U . . .
O17 O -0.5932(3) -0.1787(11) -0.4530(4) 0.098(2) Uani 1 1 d . U . . .
O18 O -0.6202(4) 0.0780(17) -0.3989(5) 0.153(4) Uani 1 1 d . U . . .
O19 O -0.7251(3) 0.0232(12) -0.4581(4) 0.106(2) Uani 1 1 d . U . . .
O20 O -0.7243(3) 0.2396(11) -0.5398(4) 0.100(2) Uani 1 1 d . U . . .
C6 C -0.3024(4) -0.1963(12) -0.7717(5) 0.077(2) Uani 1 1 d . U . . .
H6 H -0.2909 -0.2551 -0.8128 0.092 Uiso 1 1 calc R . . . .
C7 C -0.3000(3) -0.0334(10) -0.6777(4) 0.0554(19) Uani 1 1 d . U . . .
H7 H -0.2879 0.0430 -0.6405 0.066 Uiso 1 1 calc R . . . .
N14 N -0.2091(3) -0.0425(10) -0.7373(4) 0.0684(18) Uani 1 1 d . U . . .
H14A H -0.1885 -0.1492 -0.7370 0.082 Uiso 1 1 d GR . . . .
H14B H -0.2037 0.0193 -0.7755 0.082 Uiso 1 1 d GR . . . .
N15 N -0.2678(3) -0.0894(9) -0.7306(3) 0.0557(15) Uani 1 1 d . U . . .
N16 N -0.3552(3) -0.2061(12) -0.7455(5) 0.086(2) Uani 1 1 d . U . . .
N17 N -0.3507(3) -0.1037(11) -0.6873(4) 0.0707(18) Uani 1 1 d D U . . .
H17 H -0.383(2) -0.086(14) -0.663(4) 0.09(3) Uiso 1 1 d D . . . .
C1 C -0.0486(4) -0.6618(13) -0.2266(6) 0.086(3) Uani 1 1 d . U . . .
H1 H -0.0350 -0.7046 -0.1841 0.103 Uiso 1 1 calc R . . . .
C2 C -0.0501(4) -0.5153(12) -0.3227(5) 0.068(2) Uani 1 1 d . U . . .
H2 H -0.0398 -0.4421 -0.3615 0.082 Uiso 1 1 calc R . . . .
N1 N 0.0386(3) -0.4850(10) -0.2642(5) 0.082(2) Uani 1 1 d . U . . .
H1A H 0.0617 -0.5847 -0.2690 0.099 Uiso 1 1 d GR . . . .
H1B H 0.0460 -0.3985 -0.2957 0.099 Uiso 1 1 d GR . . . .
N2 N -0.0181(3) -0.5519(9) -0.2704(4) 0.0643(17) Uani 1 1 d . U . . .
N3 N -0.1007(4) -0.7022(13) -0.2512(6) 0.104(3) Uani 1 1 d . U . . .
N4 N -0.1005(3) -0.6018(12) -0.3109(5) 0.087(2) Uani 1 1 d D U . . .
H4 H -0.1298 -0.5946 -0.3382 0.104 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C3 0.041(3) 0.046(3) 0.050(4) -0.005(3) -0.001(3) 0.006(3)
C4 0.042(3) 0.047(3) 0.053(4) -0.001(3) 0.000(3) 0.003(3)
C5 0.039(4) 0.050(4) 0.057(4) 0.006(3) 0.001(3) 0.007(3)
N5 0.050(4) 0.061(4) 0.072(5) -0.015(3) -0.009(3) -0.009(3)
N6 0.033(3) 0.064(3) 0.080(5) 0.002(3) -0.008(3) -0.008(3)
N7 0.041(3) 0.052(3) 0.058(4) -0.003(3) -0.009(3) 0.000(2)
N8 0.058(4) 0.058(4) 0.065(5) 0.004(3) 0.002(4) -0.004(3)
N9 0.037(3) 0.058(3) 0.057(4) -0.001(3) -0.002(3) -0.005(2)
N10 0.030(3) 0.060(3) 0.056(4) 0.003(3) -0.003(2) 0.002(2)
N11 0.066(4) 0.092(5) 0.061(4) 0.010(4) 0.010(4) 0.014(4)
N12 0.058(4) 0.056(4) 0.114(6) 0.006(4) 0.002(4) 0.006(3)
N13 0.054(4) 0.082(4) 0.062(5) 0.021(4) -0.002(3) 0.008(3)
O1 0.059(3) 0.100(4) 0.087(4) 0.011(4) -0.021(3) -0.003(3)
O2 0.044(3) 0.102(4) 0.111(5) -0.003(4) -0.011(3) -0.021(3)
O3 0.077(4) 0.085(4) 0.068(4) 0.021(3) -0.004(3) -0.006(3)
O4 0.063(4) 0.122(5) 0.129(6) 0.052(5) -0.020(4) -0.033(3)
O5 0.095(4) 0.075(4) 0.085(5) -0.022(3) 0.012(3) 0.018(3)
O6 0.163(8) 0.170(8) 0.088(5) 0.054(6) 0.050(6) 0.061(6)
O7 0.130(6) 0.103(5) 0.175(8) 0.069(6) -0.041(6) -0.057(5)
O8 0.148(7) 0.070(4) 0.126(6) -0.035(5) 0.013(5) 0.010(4)
O9 0.081(5) 0.184(8) 0.093(5) -0.007(5) -0.030(4) -0.010(5)
O10 0.061(4) 0.107(5) 0.151(7) 0.011(5) 0.018(4) 0.036(4)
C8 0.039(3) 0.050(4) 0.056(4) 0.009(3) 0.007(3) 0.007(3)
C9 0.036(3) 0.049(4) 0.058(4) 0.005(3) 0.002(3) 0.007(3)
C10 0.043(4) 0.051(4) 0.064(5) -0.007(3) -0.008(3) 0.010(3)
N18 0.042(3) 0.066(4) 0.076(5) 0.012(4) 0.009(3) 0.001(3)
N19 0.041(3) 0.078(4) 0.066(5) -0.008(3) 0.010(3) -0.004(3)
N20 0.049(3) 0.045(3) 0.061(4) 0.005(3) 0.008(3) 0.001(2)
N21 0.058(4) 0.060(3) 0.064(4) -0.007(3) 0.002(3) -0.002(3)
N22 0.041(3) 0.053(3) 0.057(4) -0.003(3) -0.003(3) 0.004(2)
N23 0.039(3) 0.059(3) 0.054(4) -0.002(3) 0.001(3) 0.004(2)
N24 0.082(5) 0.123(6) 0.061(5) -0.023(5) -0.023(4) 0.044(5)
N25 0.065(5) 0.053(4) 0.174(9) -0.023(5) 0.028(6) 0.002(4)
N26 0.053(4) 0.074(4) 0.075(5) -0.003(4) -0.001(3) 0.010(3)
O11 0.046(3) 0.123(5) 0.139(6) -0.052(5) 0.023(4) -0.002(3)
O12 0.045(3) 0.127(5) 0.119(5) -0.023(5) 0.008(4) -0.020(3)
O13 0.075(4) 0.084(4) 0.078(5) -0.017(4) 0.001(3) 0.005(3)
O14 0.053(3) 0.123(5) 0.120(6) -0.036(5) 0.010(4) -0.026(3)
O15 0.124(7) 0.089(5) 0.228(9) 0.099(6) -0.019(7) -0.006(4)
O16 0.195(10) 0.209(11) 0.244(10) -0.163(10) 0.127(8) -0.139(9)
O17 0.101(5) 0.111(5) 0.083(5) 0.036(4) 0.009(4) 0.039(4)
O18 0.166(8) 0.205(9) 0.088(6) -0.047(6) -0.035(6) 0.073(7)
O19 0.080(5) 0.137(6) 0.101(6) 0.013(5) 0.028(4) 0.015(4)
O20 0.069(4) 0.111(5) 0.118(5) 0.005(4) -0.009(4) 0.044(3)
C6 0.075(6) 0.085(5) 0.071(6) -0.018(5) -0.005(4) -0.006(5)
C7 0.048(4) 0.059(4) 0.059(5) -0.002(4) 0.007(4) -0.002(3)
N14 0.054(4) 0.089(5) 0.062(4) 0.003(4) 0.013(3) -0.003(3)
N15 0.049(3) 0.067(4) 0.052(4) 0.003(3) 0.009(3) 0.002(3)
N16 0.069(5) 0.095(5) 0.094(5) -0.009(5) -0.008(4) -0.015(4)
N17 0.047(4) 0.081(5) 0.084(5) 0.004(4) 0.010(4) -0.001(3)
C1 0.082(6) 0.091(6) 0.086(6) 0.024(5) 0.020(5) 0.005(5)
C2 0.068(5) 0.084(5) 0.054(5) 0.005(4) -0.010(4) 0.004(4)
N1 0.072(5) 0.072(4) 0.104(7) 0.006(4) -0.019(4) -0.015(3)
N2 0.063(4) 0.074(4) 0.056(4) -0.002(4) -0.004(3) 0.005(3)
N3 0.082(5) 0.109(6) 0.121(7) 0.013(5) 0.033(5) -0.010(5)
N4 0.073(5) 0.104(6) 0.083(5) -0.028(5) 0.000(4) 0.001(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 N6 1.333(8) . ?
C3 N7 1.330(8) . ?
C3 N10 1.392(8) . ?
C4 N7 1.337(8) . ?
C4 N8 1.462(9) . ?
C4 N9 1.288(8) . ?
C5 N10 1.398(9) . ?
C5 N11 1.542(11) . ?
C5 N12 1.547(10) . ?
C5 N13 1.535(10) . ?
N5 N6 1.319(9) . ?
N5 O1 1.231(8) . ?
N5 O2 1.253(8) . ?
N8 O3 1.199(8) . ?
N8 O4 1.216(9) . ?
N9 N10 1.374(7) . ?
N11 O5 1.198(8) . ?
N11 O6 1.186(10) . ?
N12 O7 1.189(11) . ?
N12 O8 1.191(11) . ?
N13 O9 1.178(10) . ?
N13 O10 1.207(9) . ?
C8 N19 1.346(9) . ?
C8 N20 1.321(9) . ?
C8 N23 1.380(8) . ?
C9 N20 1.348(9) . ?
C9 N21 1.466(9) . ?
C9 N22 1.300(9) . ?
C10 N23 1.363(9) . ?
C10 N24 1.542(11) . ?
C10 N25 1.537(12) . ?
C10 N26 1.561(10) . ?
N18 N19 1.322(8) . ?
N18 O11 1.224(8) . ?
N18 O12 1.215(8) . ?
N21 O13 1.218(9) . ?
N21 O14 1.192(9) . ?
N22 N23 1.390(8) . ?
N24 O17 1.189(10) . ?
N24 O18 1.205(10) . ?
N25 O15 1.148(14) . ?
N25 O16 1.213(15) . ?
N26 O19 1.191(9) . ?
N26 O20 1.203(9) . ?
C6 H6 0.9300 . ?
C6 N15 1.338(10) . ?
C6 N16 1.318(12) . ?
C7 H7 0.9300 . ?
C7 N15 1.321(10) . ?
C7 N17 1.271(10) . ?
N14 H14A 0.8609 . ?
N14 H14B 0.8613 . ?
N14 N15 1.394(8) . ?
N16 N17 1.330(10) . ?
N17 H17 0.89(3) . ?
C1 H1 0.9300 . ?
C1 N2 1.330(11) . ?
C1 N3 1.318(13) . ?
C2 H2 0.9300 . ?
C2 N2 1.278(10) . ?
C2 N4 1.318(11) . ?
N1 H1A 0.8620 . ?
N1 H1B 0.8625 . ?
N1 N2 1.385(9) . ?
N3 N4 1.343(12) . ?
N4 H4 0.8600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N6 C3 N10 114.8(6) . . ?
N7 C3 N6 138.3(6) . . ?
N7 C3 N10 106.9(5) . . ?
N7 C4 N8 120.7(6) . . ?
N9 C4 N7 120.5(6) . . ?
N9 C4 N8 118.8(6) . . ?
N10 C5 N11 111.7(5) . . ?
N10 C5 N12 111.1(7) . . ?
N10 C5 N13 110.2(5) . . ?
N11 C5 N12 110.8(6) . . ?
N13 C5 N11 106.1(6) . . ?
N13 C5 N12 106.7(5) . . ?
O1 N5 N6 124.2(6) . . ?
O1 N5 O2 119.9(7) . . ?
O2 N5 N6 115.8(7) . . ?
N5 N6 C3 117.3(6) . . ?
C3 N7 C4 102.4(5) . . ?
O3 N8 C4 117.9(7) . . ?
O3 N8 O4 123.9(7) . . ?
O4 N8 C4 118.2(7) . . ?
C4 N9 N10 98.8(5) . . ?
C3 N10 C5 127.2(6) . . ?
N9 N10 C3 111.4(5) . . ?
N9 N10 C5 121.5(5) . . ?
O5 N11 C5 115.9(7) . . ?
O6 N11 C5 116.4(8) . . ?
O6 N11 O5 127.5(9) . . ?
O7 N12 C5 116.1(9) . . ?
O7 N12 O8 129.3(9) . . ?
O8 N12 C5 114.5(8) . . ?
O9 N13 C5 117.5(7) . . ?
O9 N13 O10 127.9(8) . . ?
O10 N13 C5 114.5(8) . . ?
N19 C8 N23 114.7(6) . . ?
N20 C8 N19 136.4(6) . . ?
N20 C8 N23 108.9(6) . . ?
N20 C9 N21 121.0(6) . . ?
N22 C9 N20 118.9(6) . . ?
N22 C9 N21 120.1(6) . . ?
N23 C10 N24 112.1(6) . . ?
N23 C10 N25 112.0(8) . . ?
N23 C10 N26 109.6(6) . . ?
N24 C10 N26 105.9(6) . . ?
N25 C10 N24 111.0(8) . . ?
N25 C10 N26 106.0(5) . . ?
O11 N18 N19 123.0(6) . . ?
O12 N18 N19 116.7(7) . . ?
O12 N18 O11 120.4(7) . . ?
N18 N19 C8 117.5(6) . . ?
C8 N20 C9 102.5(5) . . ?
O13 N21 C9 116.2(6) . . ?
O14 N21 C9 117.9(7) . . ?
O14 N21 O13 125.9(7) . . ?
C9 N22 N23 99.8(5) . . ?
C8 N23 N22 109.9(6) . . ?
C10 N23 C8 127.7(6) . . ?
C10 N23 N22 122.3(6) . . ?
O17 N24 C10 116.8(8) . . ?
O17 N24 O18 124.5(9) . . ?
O18 N24 C10 118.0(8) . . ?
O15 N25 C10 116.3(10) . . ?
O15 N25 O16 129.9(12) . . ?
O16 N25 C10 113.7(13) . . ?
O19 N26 C10 116.4(7) . . ?
O19 N26 O20 128.5(8) . . ?
O20 N26 C10 115.1(7) . . ?
N15 C6 H6 124.9 . . ?
N16 C6 H6 124.9 . . ?
N16 C6 N15 110.2(8) . . ?
N15 C7 H7 126.5 . . ?
N17 C7 H7 126.5 . . ?
N17 C7 N15 107.1(7) . . ?
H14A N14 H14B 109.4 . . ?
N15 N14 H14A 110.0 . . ?
N15 N14 H14B 109.3 . . ?
C6 N15 N14 130.0(7) . . ?
C7 N15 C6 106.5(7) . . ?
C7 N15 N14 123.5(7) . . ?
C6 N16 N17 103.3(7) . . ?
C7 N17 N16 113.0(7) . . ?
C7 N17 H17 130(6) . . ?
N16 N17 H17 117(6) . . ?
N2 C1 H1 124.3 . . ?
N3 C1 H1 124.3 . . ?
N3 C1 N2 111.3(9) . . ?
N2 C2 H2 126.8 . . ?
N2 C2 N4 106.4(9) . . ?
N4 C2 H2 126.8 . . ?
H1A N1 H1B 109.2 . . ?
N2 N1 H1A 108.4 . . ?
N2 N1 H1B 110.3 . . ?
C1 N2 N1 128.5(8) . . ?
C2 N2 C1 108.2(8) . . ?
C2 N2 N1 123.3(8) . . ?
C1 N3 N4 101.8(7) . . ?
C2 N4 N3 112.2(8) . . ?
C2 N4 H4 123.9 . . ?
N3 N4 H4 123.9 . . ?
_shelx_res_file
;
a.res created by SHELXL-2014/7
TITL a_a.res in Pca2(1)
REM Old TITL a in Pca21 #29
REM SHELXT solution in Pca2(1)
REM R1 0.232, Rweak 0.055, Alpha 0.009, Orientation as input
REM Flack x = 0.485 ( 0.616 ) from Parsons' quotients
REM Formula found by SHELXT: C40 N O14
CELL 0.71073 23.003 6.749 19.4216 90 90 90
ZERR 8 0.0024 0.0007 0.0023 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,-Y,+Z
SYMM 0.5-X,+Y,0.5+Z
SFAC C H N O
UNIT 40 40 104 80
DFIX 2.9 O2 N4
DFIX 2.9 O12 N17
DFIX 0.88 N17 H17
FLAT C6 C7 N15 N16 N17
DELU
ISOR O16 O15 N25
ISOR 0.01 0.02 C7
L.S. 10
PLAN 40
TEMP 23
BOND $H
LIST 6
damp
fmap 2
acta
SHEL 999 0.8
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM
REM
REM
WGHT 0.097200
BASF 0.04250
FVAR 0.40110
C3 1 -0.334594 -0.683602 -0.394906 11.00000 0.04112 0.04646 =
0.05008 -0.00522 -0.00126 0.00641
C4 1 -0.406610 -0.844341 -0.362399 11.00000 0.04239 0.04738 =
0.05304 -0.00134 -0.00045 0.00307
C5 1 -0.388342 -0.503871 -0.487594 11.00000 0.03873 0.04950 =
0.05686 0.00611 0.00131 0.00686
N5 3 -0.238706 -0.622752 -0.379004 11.00000 0.05011 0.06102 =
0.07191 -0.01467 -0.00878 -0.00866
N6 3 -0.286845 -0.585248 -0.413511 11.00000 0.03340 0.06364 =
0.08001 0.00168 -0.00772 -0.00793
N7 3 -0.350105 -0.819435 -0.348847 11.00000 0.04097 0.05166 =
0.05841 -0.00257 -0.00880 0.00030
N8 3 -0.441639 -0.982894 -0.322024 11.00000 0.05753 0.05793 =
0.06462 0.00447 0.00232 -0.00438
N9 3 -0.431142 -0.746776 -0.411417 11.00000 0.03731 0.05807 =
0.05683 -0.00126 -0.00230 -0.00503
N10 3 -0.383955 -0.639114 -0.433333 11.00000 0.03037 0.05968 =
0.05595 0.00297 -0.00285 0.00187
N11 3 -0.356143 -0.577497 -0.552387 11.00000 0.06640 0.09221 =
0.06129 0.00991 0.00992 0.01392
N12 3 -0.366064 -0.296871 -0.465787 11.00000 0.05806 0.05649 =
0.11394 0.00599 0.00204 0.00643
N13 3 -0.452195 -0.478076 -0.508755 11.00000 0.05385 0.08195 =
0.06190 0.02085 -0.00206 0.00811
O1 4 -0.235196 -0.743062 -0.331513 11.00000 0.05862 0.09967 =
0.08657 0.01059 -0.02097 -0.00291
O2 4 -0.194978 -0.523778 -0.396257 11.00000 0.04372 0.10157 =
0.11121 -0.00329 -0.01129 -0.02135
O3 4 -0.418212 -1.070928 -0.276134 11.00000 0.07701 0.08469 =
0.06779 0.02066 -0.00378 -0.00611
O4 4 -0.492714 -1.001550 -0.336775 11.00000 0.06274 0.12208 =
0.12852 0.05182 -0.02037 -0.03349
O5 4 -0.334309 -0.738159 -0.548171 11.00000 0.09509 0.07476 =
0.08516 -0.02240 0.01220 0.01816
O6 4 -0.359265 -0.475000 -0.601850 11.00000 0.16279 0.16961 =
0.08770 0.05418 0.05030 0.06112
O7 4 -0.350898 -0.190433 -0.511145 11.00000 0.12966 0.10277 =
0.17489 0.06889 -0.04107 -0.05704
O8 4 -0.369475 -0.264026 -0.405687 11.00000 0.14837 0.06982 =
0.12630 -0.03510 0.01338 0.00982
O9 4 -0.469687 -0.577682 -0.554047 11.00000 0.08052 0.18363 =
0.09333 -0.00722 -0.02956 -0.01016
O10 4 -0.479076 -0.361706 -0.473943 11.00000 0.06114 0.10697 =
0.15086 0.01110 0.01775 0.03629
C8 1 -0.585151 -0.124461 -0.606499 11.00000 0.03911 0.05014 =
0.05625 0.00907 0.00721 0.00683
C9 1 -0.657367 -0.282366 -0.640563 11.00000 0.03565 0.04908 =
0.05849 0.00532 0.00198 0.00659
C10 1 -0.637818 0.067745 -0.518645 11.00000 0.04334 0.05147 =
0.06370 -0.00673 -0.00798 0.00959
N18 3 -0.487131 -0.085485 -0.618299 11.00000 0.04181 0.06557 =
0.07613 0.01154 0.00869 0.00059
N19 3 -0.535848 -0.032808 -0.587116 11.00000 0.04117 0.07826 =
0.06634 -0.00826 0.01009 -0.00421
N20 3 -0.599811 -0.262023 -0.651636 11.00000 0.04879 0.04459 =
0.06095 0.00497 0.00759 0.00105
N21 3 -0.692211 -0.420991 -0.681494 11.00000 0.05791 0.06039 =
0.06362 -0.00718 0.00232 -0.00164
N22 3 -0.681973 -0.174825 -0.593286 11.00000 0.04116 0.05306 =
0.05695 -0.00338 -0.00284 0.00353
N23 3 -0.634271 -0.065445 -0.571245 11.00000 0.03884 0.05908 =
0.05440 -0.00154 0.00066 0.00447
N24 3 -0.612672 -0.015643 -0.450975 11.00000 0.08189 0.12279 =
0.06089 -0.02268 -0.02294 0.04381
N25 3 -0.609242 0.266547 -0.537194 11.00000 0.06455 0.05279 =
0.17357 -0.02265 0.02830 0.00224
N26 3 -0.702979 0.115147 -0.503404 11.00000 0.05305 0.07362 =
0.07488 -0.00294 -0.00114 0.01041
O11 4 -0.485375 -0.211205 -0.663647 11.00000 0.04592 0.12311 =
0.13890 -0.05220 0.02318 -0.00180
O12 4 -0.443085 -0.000439 -0.600444 11.00000 0.04544 0.12740 =
0.11855 -0.02332 0.00834 -0.01972
O13 4 -0.666091 -0.516258 -0.724850 11.00000 0.07547 0.08376 =
0.07845 -0.01705 0.00137 0.00470
O14 4 -0.742822 -0.433417 -0.668946 11.00000 0.05350 0.12280 =
0.11953 -0.03603 0.00987 -0.02626
O15 4 -0.610229 0.310501 -0.594294 11.00000 0.12435 0.08862 =
0.22787 0.09868 -0.01863 -0.00573
O16 4 -0.587526 0.350785 -0.488417 11.00000 0.19486 0.20877 =
0.24391 -0.16268 0.12657 -0.13851
O17 4 -0.593184 -0.178731 -0.452966 11.00000 0.10059 0.11072 =
0.08338 0.03557 0.00905 0.03939
O18 4 -0.620208 0.077961 -0.398908 11.00000 0.16639 0.20499 =
0.08818 -0.04688 -0.03479 0.07328
O19 4 -0.725119 0.023241 -0.458109 11.00000 0.08030 0.13722 =
0.10131 0.01331 0.02764 0.01488
O20 4 -0.724346 0.239622 -0.539792 11.00000 0.06940 0.11081 =
0.11830 0.00541 -0.00912 0.04417
C6 1 -0.302407 -0.196289 -0.771669 11.00000 0.07525 0.08529 =
0.07053 -0.01782 -0.00479 -0.00572
AFIX 43
H6 2 -0.290865 -0.255133 -0.812754 11.00000 -1.20000
AFIX 0
C7 1 -0.300032 -0.033423 -0.677691 11.00000 0.04825 0.05865 =
0.05918 -0.00220 0.00737 -0.00207
AFIX 43
H7 2 -0.287942 0.042963 -0.640497 11.00000 -1.20000
AFIX 0
N14 3 -0.209081 -0.042549 -0.737285 11.00000 0.05429 0.08878 =
0.06224 0.00319 0.01292 -0.00300
AFIX 7
H14A 2 -0.188542 -0.149182 -0.736989 11.00000 -1.20000
H14B 2 -0.203693 0.019305 -0.775549 11.00000 -1.20000
AFIX 0
N15 3 -0.267820 -0.089353 -0.730557 11.00000 0.04854 0.06666 =
0.05202 0.00296 0.00858 0.00163
N16 3 -0.355194 -0.206122 -0.745496 11.00000 0.06918 0.09510 =
0.09420 -0.00857 -0.00810 -0.01505
N17 3 -0.350669 -0.103714 -0.687252 11.00000 0.04723 0.08068 =
0.08422 0.00399 0.00993 -0.00072
H17 2 -0.382997 -0.086193 -0.663065 11.00000 0.09330
C1 1 -0.048629 -0.661756 -0.226610 11.00000 0.08223 0.09058 =
0.08557 0.02385 0.01955 0.00547
AFIX 43
H1 2 -0.034995 -0.704558 -0.184054 11.00000 -1.20000
AFIX 0
C2 1 -0.050081 -0.515269 -0.322741 11.00000 0.06778 0.08369 =
0.05383 0.00545 -0.00953 0.00403
AFIX 43
H2 2 -0.039835 -0.442144 -0.361470 11.00000 -1.20000
AFIX 0
N1 3 0.038570 -0.485013 -0.264206 11.00000 0.07235 0.07152 =
0.10353 0.00582 -0.01889 -0.01480
AFIX 7
H1A 2 0.061660 -0.584661 -0.268989 11.00000 -1.20000
H1B 2 0.046049 -0.398537 -0.295684 11.00000 -1.20000
AFIX 0
N2 3 -0.018089 -0.551891 -0.270444 11.00000 0.06289 0.07420 =
0.05581 -0.00202 -0.00407 0.00459
N3 3 -0.100689 -0.702219 -0.251193 11.00000 0.08214 0.10865 =
0.12125 0.01282 0.03346 -0.01026
N4 3 -0.100488 -0.601757 -0.310866 11.00000 0.07284 0.10401 =
0.08332 -0.02780 0.00001 0.00098
AFIX 43
H4 2 -0.129841 -0.594649 -0.338179 11.00000 -1.20000
AFIX 0
HKLF 4
REM a_a.res in Pca2(1)
REM R1 = 0.0602 for 3165 Fo > 4sig(Fo) and 0.1222 for all 5696 data
REM 512 parameters refined using 166 restraints
END
WGHT 0.0971 0.0000
REM Highest difference peak 0.468, deepest hole -0.244, 1-sigma level 0.052
Q1 1 -0.5797 0.1728 -0.4400 11.00000 0.05 0.47
Q2 1 -0.3251 -0.3975 -0.5676 11.00000 0.05 0.30
Q3 1 0.0093 -0.4712 -0.2195 11.00000 0.05 0.28
Q4 1 -0.3658 -0.1832 -0.3503 11.00000 0.05 0.24
Q5 1 -0.2659 -0.4039 -0.3911 11.00000 0.05 0.23
Q6 1 0.0090 -0.3987 -0.2956 11.00000 0.05 0.23
Q7 1 -0.4496 -0.2643 -0.4160 11.00000 0.05 0.22
Q8 1 -0.4216 -0.1907 -0.3703 11.00000 0.05 0.21
Q9 1 -0.4667 -0.6594 -0.4799 11.00000 0.05 0.21
Q10 1 -0.6296 0.3168 -0.6488 11.00000 0.05 0.21
Q11 1 0.0407 -0.3731 -0.2212 11.00000 0.05 0.21
Q12 1 -0.7183 -0.1005 -0.5031 11.00000 0.05 0.20
Q13 1 -0.4216 -0.3012 -0.7464 11.00000 0.05 0.20
Q14 1 -0.1678 -0.8055 -0.2547 11.00000 0.05 0.20
Q15 1 -0.5800 0.3581 -0.4715 11.00000 0.05 0.20
Q16 1 -0.4066 -0.3885 -0.4274 11.00000 0.05 0.20
Q17 1 -0.3168 -0.3622 -0.3958 11.00000 0.05 0.20
Q18 1 -0.6503 0.2550 -0.5971 11.00000 0.05 0.20
Q19 1 -0.3803 -0.9700 -0.2682 11.00000 0.05 0.19
Q20 1 -0.2491 -0.3006 -0.8298 11.00000 0.05 0.19
Q21 1 -0.0252 -0.8463 -0.1694 11.00000 0.05 0.18
Q22 1 -0.4925 0.1041 -0.6204 11.00000 0.05 0.18
Q23 1 -0.7093 -0.5883 -0.6902 11.00000 0.05 0.18
Q24 1 -0.2232 -0.0367 -0.7933 11.00000 0.05 0.17
Q25 1 -0.4196 -0.1828 -0.4235 11.00000 0.05 0.17
Q26 1 -0.6861 -0.4886 -0.7304 11.00000 0.05 0.17
Q27 1 -0.4900 -0.5629 -0.4893 11.00000 0.05 0.17
Q28 1 -0.0396 -0.4120 -0.2605 11.00000 0.05 0.17
Q29 1 -0.6468 -0.4451 -0.7322 11.00000 0.05 0.17
Q30 1 -0.2524 0.0628 -0.7250 11.00000 0.05 0.17
Q31 1 -0.0577 -0.6309 -0.2778 11.00000 0.05 0.16
Q32 1 -0.6706 -0.5493 -0.6816 11.00000 0.05 0.16
Q33 1 -0.4488 -0.4585 -0.5680 11.00000 0.05 0.16
Q34 1 -0.2109 -0.1819 -0.7782 11.00000 0.05 0.16
Q35 1 -0.1201 -0.3992 -0.3147 11.00000 0.05 0.16
Q36 1 -0.4234 0.0343 -0.5685 11.00000 0.05 0.16
Q37 1 -0.5623 0.1619 -0.5958 11.00000 0.05 0.15
Q38 1 -0.3241 -0.1840 -0.3509 11.00000 0.05 0.15
Q39 1 -0.5767 0.3121 -0.6441 11.00000 0.05 0.15
Q40 1 -0.3815 -0.3137 -0.7706 11.00000 0.05 0.15
;
_shelx_res_checksum 9660
_shelx_SHELXL_version_number 2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(3)
2 0(3)
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_a
_database_code_depnum_ccdc_archive 'CCDC 1502834'
_audit_update_record
;
2016-12-26 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date 2016-12-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.12.12 svn.r3370 for OlexSys, GUI svn.r5282)
;
_shelxl_version_number 2014-3
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C3 N9 O10, C H4 N5'
_chemical_formula_sum 'C4 H4 N14 O10'
_chemical_formula_weight 408.21
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'C 1 2/c 1'
_space_group_name_Hall '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 12.264(5)
_cell_length_b 20.048(7)
_cell_length_c 12.605(5)
_cell_angle_alpha 90
_cell_angle_beta 98.056(17)
_cell_angle_gamma 90
_cell_volume 3069(2)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 1434
_cell_measurement_temperature 296.15
_cell_measurement_theta_max 24.927
_cell_measurement_theta_min 2.396
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.169
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.4587
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1637 before and 0.0766 after correction. The Ratio of minimum to maximum transmission is 0.6152. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour 'clear whiteish colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier whiteish
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.767
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1648
_exptl_crystal_size_max 0.3
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.12
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0942
_diffrn_reflns_av_unetI/netI 0.0991
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 8923
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 25.003
_diffrn_reflns_theta_min 1.961
_diffrn_ambient_temperature 296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1494
_reflns_number_total 2668
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection ?
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max 0.344
_refine_diff_density_min -0.222
_refine_diff_density_rms 0.058
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.001
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 317
_refine_ls_number_reflns 2668
_refine_ls_number_restraints 132
_refine_ls_R_factor_all 0.1142
_refine_ls_R_factor_gt 0.0534
_refine_ls_restrained_S_all 0.995
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0595P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1195
_refine_ls_wR_factor_ref 0.1469
_refine_special_details
;
?
;
_olex2_refinement_description
;
1. Rigid bond restraints
All non-hydrogen atoms
with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
2. Uiso/Uaniso restraints and constraints
Uanis(N12A) \\sim Ueq, Uanis(N13A) \\sim Ueq, Uanis(N14A) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(O9A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O5A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N12) \\sim Ueq, Uanis(N13) \\sim Ueq, Uanis(N14) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
3. Others
Sof(N14A)=Sof(N13A)=Sof(N12A)=1-FVAR(1)
Sof(N14)=Sof(N12)=Sof(N13)=FVAR(1)
Sof(O9A)=1-FVAR(2)
Sof(O9)=FVAR(2)
Sof(O5A)=1-FVAR(3)
Sof(O5)=FVAR(3)
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.62275(19) 0.20716(12) 0.73619(18) 0.0530(7) Uani 1 1 d . U . . .
O3 O 0.7369(2) 0.28167(12) 0.81051(18) 0.0622(8) Uani 1 1 d . U . . .
N2 N 0.75187(19) 0.39915(13) 0.7150(2) 0.0376(6) Uani 1 1 d . U . . .
N5 N 0.6346(2) 0.30117(14) 0.6498(2) 0.0413(7) Uani 1 1 d . U . . .
N6 N 0.6671(2) 0.26364(15) 0.7345(2) 0.0418(7) Uani 1 1 d . U . . .
N3 N 0.6483(2) 0.39944(14) 0.5572(2) 0.0408(7) Uani 1 1 d . U . . .
N4 N 0.7013(2) 0.46061(14) 0.5637(2) 0.0448(7) Uani 1 1 d . U . . .
O1 O 0.8696(2) 0.50711(14) 0.7951(2) 0.0775(9) Uani 1 1 d . U . . .
N10 N 0.3354(3) 0.18504(17) 0.5285(3) 0.0542(8) Uani 1 1 d . U . . .
N1 N 0.8312(2) 0.51039(16) 0.7007(3) 0.0529(8) Uani 1 1 d . U . . .
N8 N 0.5780(3) 0.43445(19) 0.3788(2) 0.0578(9) Uani 1 1 d . U . . .
O2 O 0.8479(3) 0.55418(16) 0.6405(3) 0.0871(10) Uani 1 1 d . U . . .
N7 N 0.6114(3) 0.31311(18) 0.4201(3) 0.0645(9) Uani 1 1 d . U . . .
C2 C 0.6810(2) 0.36230(17) 0.6491(2) 0.0358(7) Uani 1 1 d . U . . .
C4 C 0.4177(2) 0.15688(16) 0.4923(2) 0.0378(8) Uani 1 1 d . U . . .
C1 C 0.7587(2) 0.45540(16) 0.6583(3) 0.0385(8) Uani 1 1 d . U . . .
N9 N 0.4556(3) 0.37327(19) 0.4822(3) 0.0669(10) Uani 1 1 d . U . . .
C3 C 0.5768(3) 0.38052(17) 0.4648(2) 0.0435(8) Uani 1 1 d . U . . .
O6 O 0.7072(2) 0.30384(15) 0.4273(3) 0.0803(9) Uani 1 1 d . U . . .
O5 O 0.5368(3) 0.2738(2) 0.3889(3) 0.0967(17) Uani 0.859(8) 1 d . U P A 1
O7 O 0.6386(3) 0.4237(2) 0.3150(3) 0.1045(12) Uani 1 1 d . U . . .
O8 O 0.5195(3) 0.48089(18) 0.3844(2) 0.0925(11) Uani 1 1 d . U . . .
O9 O 0.3882(3) 0.3715(4) 0.3986(4) 0.102(3) Uani 0.821(14) 1 d . U P B 1
O10 O 0.4348(2) 0.37665(16) 0.5698(3) 0.0841(9) Uani 1 1 d . U . . .
N11 N 0.4193(2) 0.12932(15) 0.3974(2) 0.0468(8) Uani 1 1 d . U . . .
N14 N 0.5186(11) 0.1460(8) 0.5471(9) 0.042(2) Uani 0.63(4) 1 d . U P C 1
N12 N 0.5211(8) 0.0993(8) 0.3976(10) 0.052(2) Uani 0.63(4) 1 d . U P C 1
N13 N 0.5821(7) 0.1125(8) 0.4847(9) 0.054(3) Uani 0.63(4) 1 d . U P C 1
N14A N 0.5266(17) 0.1616(11) 0.5313(18) 0.040(4) Uani 0.37(4) 1 d . U P C 2
N13A N 0.5865(12) 0.1364(13) 0.4614(15) 0.054(4) Uani 0.37(4) 1 d . U P C 2
N12A N 0.5238(13) 0.1209(12) 0.3746(14) 0.047(4) Uani 0.37(4) 1 d . U P C 2
H10A H 0.339(3) 0.1916(19) 0.601(4) 0.068(12) Uiso 1 1 d . . . . .
H10B H 0.268(4) 0.179(2) 0.490(4) 0.101(17) Uiso 1 1 d . . . . .
H11 H 0.362(3) 0.122(2) 0.340(3) 0.079(13) Uiso 1 1 d . . . . .
H14 H 0.557(5) 0.166(3) 0.615(5) 0.13(2) Uiso 1 1 d . . . . .
O9A O 0.417(2) 0.3226(18) 0.432(2) 0.109(8) Uani 0.179(14) 1 d . U P B 2
O5A O 0.580(2) 0.3140(12) 0.3153(17) 0.082(7) Uani 0.141(8) 1 d . U P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0672(15) 0.0490(17) 0.0390(13) 0.0041(11) -0.0055(11) -0.0224(13)
O3 0.0759(16) 0.0642(19) 0.0379(13) 0.0089(12) -0.0218(13) -0.0272(14)
N2 0.0357(13) 0.0402(18) 0.0352(14) -0.0001(12) -0.0012(12) 0.0002(11)
N5 0.0429(14) 0.0464(19) 0.0315(14) 0.0090(12) -0.0065(12) -0.0067(13)
N6 0.0433(14) 0.048(2) 0.0324(14) 0.0031(13) 0.0006(12) -0.0074(13)
N3 0.0397(14) 0.0449(19) 0.0354(14) 0.0073(12) -0.0035(12) -0.0019(12)
N4 0.0366(13) 0.047(2) 0.0488(16) 0.0100(13) 0.0001(13) 0.0031(12)
O1 0.088(2) 0.068(2) 0.0674(19) -0.0033(15) -0.0212(17) -0.0205(15)
N10 0.0557(19) 0.068(2) 0.0392(18) -0.0051(15) 0.0079(16) 0.0158(16)
N1 0.0452(16) 0.047(2) 0.063(2) 0.0073(16) -0.0076(15) -0.0025(13)
N8 0.0582(19) 0.072(3) 0.0390(17) 0.0112(16) -0.0081(15) -0.0053(17)
O2 0.097(2) 0.061(2) 0.096(2) 0.0301(18) -0.0132(19) -0.0264(17)
N7 0.072(2) 0.069(3) 0.0471(18) -0.0054(16) -0.0104(18) 0.0030(19)
C2 0.0326(15) 0.043(2) 0.0308(16) 0.0049(14) 0.0005(13) 0.0024(14)
C4 0.0417(16) 0.036(2) 0.0350(17) -0.0001(14) 0.0018(14) 0.0025(14)
C1 0.0335(15) 0.038(2) 0.0426(18) 0.0062(15) -0.0013(14) 0.0031(13)
N9 0.0451(17) 0.088(3) 0.065(2) 0.010(2) 0.0012(18) -0.0093(16)
C3 0.0415(16) 0.052(2) 0.0339(17) 0.0044(15) -0.0048(14) 0.0014(14)
O6 0.0713(19) 0.086(2) 0.085(2) -0.0130(17) 0.0151(17) 0.0210(16)
O5 0.112(3) 0.076(3) 0.095(3) -0.022(2) -0.015(2) -0.032(2)
O7 0.104(2) 0.150(3) 0.065(2) 0.042(2) 0.0286(19) 0.009(2)
O8 0.121(3) 0.076(2) 0.073(2) 0.0158(17) -0.016(2) 0.028(2)
O9 0.048(2) 0.155(7) 0.091(3) 0.012(3) -0.031(2) -0.011(2)
O10 0.0564(16) 0.112(3) 0.088(2) 0.0170(19) 0.0258(17) 0.0111(16)
N11 0.0384(14) 0.061(2) 0.0390(16) -0.0161(14) -0.0003(13) 0.0036(13)
N14 0.042(3) 0.047(5) 0.036(3) 0.005(3) -0.008(2) -0.004(3)
N12 0.046(3) 0.055(5) 0.055(4) -0.009(3) 0.006(3) 0.007(3)
N13 0.042(3) 0.060(5) 0.057(4) -0.002(3) -0.004(3) 0.004(3)
N14A 0.040(4) 0.036(6) 0.040(5) -0.002(4) -0.006(4) -0.008(4)
N13A 0.045(4) 0.060(6) 0.057(5) -0.001(4) 0.001(3) -0.003(4)
N12A 0.043(4) 0.052(6) 0.047(5) -0.007(4) 0.004(3) 0.003(4)
O9A 0.094(10) 0.105(11) 0.121(11) -0.008(8) -0.011(8) -0.030(8)
O5A 0.101(10) 0.084(11) 0.058(7) -0.017(7) -0.001(7) 0.020(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 N6 1.257(3) . ?
O3 N6 1.246(3) . ?
N2 C2 1.337(4) . ?
N2 C1 1.344(4) . ?
N5 N6 1.321(4) . ?
N5 C2 1.352(4) . ?
N3 N4 1.385(4) . ?
N3 C2 1.389(4) . ?
N3 C3 1.408(4) . ?
N4 C1 1.302(4) . ?
O1 N1 1.220(4) . ?
N10 C4 1.295(4) . ?
N10 H10A 0.92(4) . ?
N10 H10B 0.91(5) . ?
N1 O2 1.197(4) . ?
N1 C1 1.468(4) . ?
N8 C3 1.533(5) . ?
N8 O7 1.189(4) . ?
N8 O8 1.184(4) . ?
N7 C3 1.547(5) . ?
N7 O6 1.180(4) . ?
N7 O5 1.230(5) . ?
N7 O5A 1.32(2) . ?
C4 N11 1.319(4) . ?
C4 N14 1.348(12) . ?
C4 N14A 1.36(2) . ?
N9 C3 1.539(5) . ?
N9 O9 1.245(5) . ?
N9 O10 1.169(4) . ?
N9 O9A 1.25(2) . ?
N11 N12 1.386(10) . ?
N11 N12A 1.364(16) . ?
N11 H11 0.94(4) . ?
N14 N13 1.360(14) . ?
N14 H14 1.00(6) . ?
N12 N13 1.267(11) . ?
N14A N13A 1.32(3) . ?
N14A H14 1.07(6) . ?
N13A N12A 1.284(19) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N2 C1 102.5(3) . . ?
N6 N5 C2 116.2(3) . . ?
O4 N6 N5 116.4(3) . . ?
O3 N6 O4 120.0(3) . . ?
O3 N6 N5 123.6(3) . . ?
N4 N3 C2 110.3(2) . . ?
N4 N3 C3 121.4(2) . . ?
C2 N3 C3 128.3(3) . . ?
C1 N4 N3 99.9(2) . . ?
C4 N10 H10A 119(2) . . ?
C4 N10 H10B 117(3) . . ?
H10A N10 H10B 118(4) . . ?
O1 N1 C1 116.5(3) . . ?
O2 N1 O1 125.6(3) . . ?
O2 N1 C1 118.0(3) . . ?
O7 N8 C3 114.8(3) . . ?
O8 N8 C3 116.5(3) . . ?
O8 N8 O7 128.7(4) . . ?
O6 N7 C3 115.5(3) . . ?
O6 N7 O5 127.8(4) . . ?
O6 N7 O5A 103.2(11) . . ?
O5 N7 C3 116.5(4) . . ?
O5A N7 C3 107.2(10) . . ?
N2 C2 N5 137.2(3) . . ?
N2 C2 N3 108.0(3) . . ?
N5 C2 N3 114.8(3) . . ?
N10 C4 N11 127.9(3) . . ?
N10 C4 N14 126.5(6) . . ?
N10 C4 N14A 128.1(9) . . ?
N11 C4 N14 105.5(6) . . ?
N11 C4 N14A 102.6(9) . . ?
N2 C1 N1 121.1(3) . . ?
N4 C1 N2 119.2(3) . . ?
N4 C1 N1 119.7(3) . . ?
O9 N9 C3 115.0(4) . . ?
O10 N9 C3 118.1(3) . . ?
O10 N9 O9 126.4(4) . . ?
O10 N9 O9A 114.0(13) . . ?
O9A N9 C3 107.8(12) . . ?
N3 C3 N8 109.2(3) . . ?
N3 C3 N7 111.5(3) . . ?
N3 C3 N9 114.2(3) . . ?
N8 C3 N7 109.1(3) . . ?
N8 C3 N9 105.8(3) . . ?
N9 C3 N7 106.8(3) . . ?
C4 N11 N12 107.9(5) . . ?
C4 N11 N12A 112.2(7) . . ?
C4 N11 H11 131(3) . . ?
N12 N11 H11 120(3) . . ?
N12A N11 H11 116(3) . . ?
C4 N14 N13 110.1(8) . . ?
C4 N14 H14 131(3) . . ?
N13 N14 H14 117(3) . . ?
N13 N12 N11 109.5(7) . . ?
N12 N13 N14 106.7(8) . . ?
C4 N14A H14 123(4) . . ?
N13A N14A C4 109.9(15) . . ?
N13A N14A H14 123(4) . . ?
N12A N13A N14A 109.7(15) . . ?
N13A N12A N11 105.0(12) . . ?
_shelx_res_file
;
TITL a_a.res in C2/c
REM Old TITL a in C2/c #15
REM SHELXT solution in C2/c
REM R1 0.264, Rweak 0.060, Alpha 0.055, Orientation as input
REM Formula found by SHELXT: C20 O8
CELL 0.71073 12.2642 20.0478 12.605 90 98.056 90
ZERR 8 0.0047 0.0069 0.0047 0 0.017 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O
UNIT 32 32 112 80
DELU
ISOR 0.005 0.01 N12A N13A N14A
ISOR 0.005 0.01 O9A
ISOR 0.005 0.01 O5A
ISOR 0.005 0.01 N12 N13 N14
L.S. 10
PLAN 20
TEMP 23
damp
BOND $H
LIST 6
fmap 2 53
acta
SHEL 999 0.837
OMIT -1 1 1
OMIT -2 6 6
OMIT 0 14 6
OMIT -7 5 6
OMIT 0 0 2
OMIT 0 8 0
OMIT 0 6 4
OMIT 1 13 0
OMIT 1 13 4
OMIT -4 2 5
OMIT -3 5 4
OMIT -3 1 4
OMIT 3 1 0
OMIT 1 5 3
OMIT 3 9 1
OMIT 1 5 0
OMIT 0 0 6
OMIT 4 2 0
OMIT 0 18 6
OMIT 0 4 0
OMIT -7 1 5
OMIT 1 1 4
OMIT 2 12 3
OMIT -2 0 2
REM
REM
REM
WGHT 0.059500
FVAR 0.09303 0.62823 0.82072 0.85866
O4 4 0.622750 0.207164 0.736191 11.00000 0.06716 0.04904 =
0.03898 0.00407 -0.00550 -0.02240
O3 4 0.736888 0.281666 0.810514 11.00000 0.07592 0.06419 =
0.03789 0.00893 -0.02176 -0.02717
N2 3 0.751874 0.399148 0.714990 11.00000 0.03567 0.04024 =
0.03524 -0.00008 -0.00123 0.00022
N5 3 0.634572 0.301171 0.649832 11.00000 0.04286 0.04636 =
0.03148 0.00898 -0.00646 -0.00667
N6 3 0.667062 0.263644 0.734507 11.00000 0.04327 0.04848 =
0.03238 0.00308 0.00058 -0.00738
N3 3 0.648287 0.399440 0.557168 11.00000 0.03971 0.04492 =
0.03536 0.00734 -0.00346 -0.00186
N4 3 0.701317 0.460610 0.563687 11.00000 0.03657 0.04734 =
0.04875 0.00997 0.00011 0.00314
O1 4 0.869631 0.507107 0.795123 11.00000 0.08842 0.06760 =
0.06740 -0.00332 -0.02117 -0.02046
N10 3 0.335373 0.185044 0.528509 11.00000 0.05570 0.06815 =
0.03918 -0.00511 0.00790 0.01578
N1 3 0.831168 0.510388 0.700660 11.00000 0.04521 0.04659 =
0.06264 0.00725 -0.00758 -0.00250
N8 3 0.578011 0.434450 0.378757 11.00000 0.05816 0.07205 =
0.03896 0.01122 -0.00808 -0.00535
O2 4 0.847857 0.554180 0.640462 11.00000 0.09719 0.06077 =
0.09581 0.03008 -0.01321 -0.02637
N7 3 0.611428 0.313108 0.420071 11.00000 0.07202 0.06905 =
0.04710 -0.00535 -0.01041 0.00301
C2 1 0.681011 0.362298 0.649099 11.00000 0.03258 0.04301 =
0.03082 0.00488 0.00048 0.00240
C4 1 0.417672 0.156880 0.492251 11.00000 0.04171 0.03567 =
0.03496 -0.00008 0.00176 0.00246
C1 1 0.758736 0.455404 0.658310 11.00000 0.03349 0.03760 =
0.04258 0.00616 -0.00134 0.00313
N9 3 0.455595 0.373270 0.482177 11.00000 0.04508 0.08844 =
0.06537 0.01007 0.00123 -0.00933
C3 1 0.576770 0.380515 0.464812 11.00000 0.04146 0.05219 =
0.03393 0.00437 -0.00483 0.00145
O6 4 0.707194 0.303842 0.427344 11.00000 0.07128 0.08581 =
0.08510 -0.01295 0.01514 0.02096
PART 1
O5 4 0.536765 0.273795 0.388933 41.00000 0.11169 0.07554 =
0.09451 -0.02184 -0.01499 -0.03159
PART 0
O7 4 0.638619 0.423689 0.314980 11.00000 0.10391 0.14968 =
0.06461 0.04191 0.02859 0.00853
O8 4 0.519468 0.480886 0.384390 11.00000 0.12067 0.07592 =
0.07255 0.01578 -0.01573 0.02804
PART 1
O9 4 0.388222 0.371523 0.398630 31.00000 0.04759 0.15548 =
0.09061 0.01161 -0.03065 -0.01124
PART 0
O10 4 0.434774 0.376648 0.569761 11.00000 0.05643 0.11182 =
0.08840 0.01696 0.02580 0.01110
N11 3 0.419266 0.129318 0.397445 11.00000 0.03844 0.06126 =
0.03901 -0.01610 -0.00029 0.00361
PART 1
N14 3 0.518582 0.146046 0.547063 21.00000 0.04155 0.04652 =
0.03558 0.00520 -0.00808 -0.00373
N12 3 0.521137 0.099318 0.397601 21.00000 0.04622 0.05538 =
0.05451 -0.00922 0.00584 0.00670
N13 3 0.582135 0.112505 0.484721 21.00000 0.04245 0.05982 =
0.05712 -0.00227 -0.00423 0.00362
PART 0
PART 2
N14A 3 0.526636 0.161567 0.531309 -21.00000 0.04018 0.03594 =
0.04044 -0.00235 -0.00565 -0.00755
N13A 3 0.586528 0.136435 0.461352 -21.00000 0.04477 0.05986 =
0.05688 -0.00135 0.00135 -0.00320
N12A 3 0.523811 0.120878 0.374584 -21.00000 0.04298 0.05189 =
0.04666 -0.00667 0.00449 0.00264
PART 0
H10A 2 0.338989 0.191617 0.600998 11.00000 0.06846
H10B 2 0.267962 0.179348 0.489569 11.00000 0.10058
H11 2 0.362355 0.122259 0.339930 11.00000 0.07890
H14 2 0.556777 0.166394 0.614759 11.00000 0.13355
PART 2
O9A 4 0.417268 0.322626 0.432047 -31.00000 0.09448 0.10527 =
0.12096 -0.00835 -0.01072 -0.02975
O5A 4 0.579911 0.313970 0.315259 -41.00000 0.10148 0.08384 =
0.05802 -0.01696 -0.00089 0.01971
HKLF 4
REM a_a.res in C2/c
REM R1 = 0.0534 for 1494 Fo > 4sig(Fo) and 0.1142 for all 2668 data
REM 317 parameters refined using 132 restraints
END
WGHT 0.0654 0.0000
REM Highest difference peak 0.344, deepest hole -0.222, 1-sigma level 0.058
Q1 1 0.6525 0.3429 0.3795 11.00000 0.05 0.34
Q2 1 0.4529 0.4196 0.5381 11.00000 0.05 0.23
Q3 1 0.5280 0.1593 0.3399 11.00000 0.05 0.22
Q4 1 0.8062 0.4827 0.8265 11.00000 0.05 0.21
Q5 1 0.6405 0.4768 0.3465 11.00000 0.05 0.21
Q6 1 0.4258 0.2989 0.4868 11.00000 0.05 0.19
Q7 1 0.5769 0.1776 0.4164 11.00000 0.05 0.19
Q8 1 0.7001 0.3979 0.3226 11.00000 0.05 0.19
Q9 1 0.4763 0.3848 0.6322 11.00000 0.05 0.19
Q10 1 0.6599 0.2823 0.4526 11.00000 0.05 0.18
Q11 1 0.6177 0.1971 0.8096 11.00000 0.05 0.18
Q12 1 0.6814 0.2962 0.6068 11.00000 0.05 0.18
Q13 1 0.5895 0.1768 0.7829 11.00000 0.05 0.17
Q14 1 0.4258 0.3622 0.5603 11.00000 0.05 0.17
Q15 1 0.6714 0.2827 0.8461 11.00000 0.05 0.17
Q16 1 0.5887 0.3620 0.2874 11.00000 0.05 0.17
Q17 1 0.6224 0.1565 0.6983 11.00000 0.05 0.16
Q18 1 0.7241 0.2720 0.8956 11.00000 0.05 0.16
Q19 1 0.5000 0.2638 0.7500 10.50000 0.05 0.16
Q20 1 0.6351 0.1799 0.7488 11.00000 0.05 0.16
;
_shelx_res_checksum 5531
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_a
_database_code_depnum_ccdc_archive 'CCDC 1502830'
_audit_update_record
;
2016-09-06 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date 2016-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C3 N9 O10, C2 H6 N5'
_chemical_formula_sum 'C5 H6 N14 O10'
_chemical_formula_weight 422.24
_chemical_absolute_configuration ?
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 29
_space_group_name_H-M_alt 'P c a 21'
_space_group_name_Hall 'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
_cell_length_a 9.2722(11)
_cell_length_b 13.4860(16)
_cell_length_c 12.5676(15)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1571.5(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 1674
_cell_measurement_temperature 296.15
_cell_measurement_theta_max 20.869
_cell_measurement_theta_min 2.666
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.168
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear yellowish yellow'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier yellowish
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.785
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 856
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.18
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0332
_diffrn_reflns_av_unetI/netI 0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 8984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.496
_diffrn_reflns_theta_min 2.666
_diffrn_ambient_temperature 296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.909
_reflns_Friedel_fraction_full 1.000
_reflns_Friedel_fraction_max 0.991
_reflns_number_gt 2425
_reflns_number_total 3474
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection ?
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.157
_refine_diff_density_min -0.193
_refine_diff_density_rms 0.037
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack 2(2)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.008
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 287
_refine_ls_number_reflns 3474
_refine_ls_number_restraints 7
_refine_ls_R_factor_all 0.0726
_refine_ls_R_factor_gt 0.0432
_refine_ls_restrained_S_all 1.010
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0818
_refine_ls_wR_factor_ref 0.0927
_refine_special_details
;
Refined as a 2-component inversion twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
Scales: -1(2) 2(2)
2. Uiso/Uaniso restraints and constraints
Uanis(N10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.5850(4) -0.7774(3) -0.5856(3) 0.0348(8) Uani 1 1 d . . . . .
C2 C -0.7379(4) -0.7497(3) -0.4678(3) 0.0351(8) Uani 1 1 d . . . . .
C3 C -0.9049(4) -0.8856(3) -0.5272(3) 0.0480(10) Uani 1 1 d . . . . .
N1 N -0.4558(4) -0.7673(2) -0.6499(3) 0.0414(8) Uani 1 1 d . . . . .
N2 N -0.7882(3) -0.6604(2) -0.3195(3) 0.0375(7) Uani 1 1 d . . . . .
N3 N -0.8369(3) -0.7166(2) -0.3967(2) 0.0399(8) Uani 1 1 d . . . . .
N4 N -0.9055(4) -0.9559(3) -0.4305(3) 0.0608(11) Uani 1 1 d . . . . .
N5 N -1.0409(4) -0.8196(3) -0.5230(3) 0.0636(11) Uani 1 1 d . . . . .
N6 N -0.9132(6) -0.9526(4) -0.6259(4) 0.0777(14) Uani 1 1 d . . . . .
N7 N -0.6094(3) -0.7190(2) -0.4999(2) 0.0355(7) Uani 1 1 d . . . . .
N8 N -0.7801(3) -0.8262(2) -0.5335(3) 0.0429(8) Uani 1 1 d . . . . .
N9 N -0.6805(3) -0.8433(2) -0.6123(3) 0.0418(8) Uani 1 1 d . . . . .
O1 O -0.4508(3) -0.8106(2) -0.7345(2) 0.0540(8) Uani 1 1 d . . . . .
O2 O -0.3608(3) -0.7152(3) -0.6155(3) 0.0713(10) Uani 1 1 d . . . . .
O3 O -0.6588(3) -0.6494(3) -0.2979(3) 0.0705(10) Uani 1 1 d . . . . .
O4 O -0.8829(3) -0.61777(19) -0.2642(2) 0.0449(7) Uani 1 1 d . . . . .
O5 O -1.0361(4) -0.7477(3) -0.5813(3) 0.0852(12) Uani 1 1 d . . . . .
O6 O -1.1371(3) -0.8442(3) -0.4651(3) 0.0886(12) Uani 1 1 d . . . . .
O7 O -0.8164(4) -0.9410(3) -0.3635(3) 0.0675(9) Uani 1 1 d . . . . .
O8 O -0.9953(5) -1.0216(3) -0.4360(4) 0.1034(14) Uani 1 1 d . . . . .
O9 O -0.8352(6) -1.0238(4) -0.6230(4) 0.1095(17) Uani 1 1 d . . . . .
O10 O -0.9942(6) -0.9274(5) -0.6939(4) 0.129(2) Uani 1 1 d . . . . .
C4 C -0.2953(4) -0.6188(3) -0.3686(4) 0.0465(10) Uani 1 1 d . . . . .
C5 C -0.2831(4) -0.5231(3) -0.5078(3) 0.0387(9) Uani 1 1 d . . . . .
N10 N -0.3461(5) -0.6750(4) -0.2915(4) 0.0817(16) Uani 1 1 d . U . . .
H10A H -0.434(7) -0.679(4) -0.292(5) 0.093(19) Uiso 1 1 d . . . . .
H10B H -0.282(8) -0.712(4) -0.246(5) 0.12(2) Uiso 1 1 d . . . . .
N11 N -0.3298(5) -0.4719(3) -0.5924(4) 0.0624(12) Uani 1 1 d . . . . .
H11A H -0.271(6) -0.449(4) -0.633(4) 0.060(16) Uiso 1 1 d . . . . .
H11B H -0.418(5) -0.461(3) -0.597(3) 0.048(13) Uiso 1 1 d . . . . .
N12 N -0.3753(3) -0.5714(3) -0.4408(3) 0.0391(8) Uani 1 1 d . . . . .
H12 H -0.466(7) -0.580(4) -0.444(5) 0.097(19) Uiso 1 1 d . . . . .
N13 N -0.1495(3) -0.5351(3) -0.4790(3) 0.0535(10) Uani 1 1 d . . . . .
N14 N -0.1606(4) -0.5969(3) -0.3907(4) 0.0606(11) Uani 1 1 d . . . . .
H14 H -0.083(6) -0.614(4) -0.355(4) 0.083(17) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0326(19) 0.035(2) 0.036(2) 0.0034(17) 0.0039(16) 0.0000(17)
C2 0.0281(18) 0.041(2) 0.036(2) -0.0012(16) -0.0050(15) -0.0094(15)
C3 0.048(2) 0.061(3) 0.035(2) -0.007(2) -0.0005(18) -0.025(2)
N1 0.0355(19) 0.0435(19) 0.045(2) 0.0076(16) 0.0046(15) 0.0043(15)
N2 0.0298(17) 0.0467(19) 0.0361(17) 0.0002(15) 0.0011(14) -0.0022(15)
N3 0.0272(15) 0.054(2) 0.0380(18) -0.0111(16) -0.0002(14) -0.0084(14)
N4 0.063(2) 0.064(3) 0.055(2) 0.006(2) 0.007(2) -0.021(2)
N5 0.046(2) 0.096(3) 0.049(2) 0.004(2) -0.0112(19) -0.025(2)
N6 0.083(3) 0.092(4) 0.058(3) -0.022(3) 0.007(3) -0.050(3)
N7 0.0259(14) 0.0399(16) 0.0406(18) -0.0023(14) 0.0007(13) -0.0042(13)
N8 0.0388(17) 0.055(2) 0.0351(18) -0.0062(16) 0.0043(15) -0.0206(15)
N9 0.0455(18) 0.047(2) 0.0330(17) -0.0011(15) 0.0051(15) -0.0106(16)
O1 0.0591(19) 0.0596(18) 0.0433(18) -0.0056(14) 0.0105(13) 0.0066(15)
O2 0.0401(16) 0.098(3) 0.075(2) -0.024(2) 0.0172(16) -0.0231(17)
O3 0.0289(15) 0.119(3) 0.064(2) -0.039(2) -0.0128(14) 0.0000(16)
O4 0.0371(15) 0.0529(16) 0.0448(16) -0.0069(14) 0.0017(12) 0.0019(13)
O5 0.066(2) 0.109(3) 0.081(3) 0.028(2) -0.026(2) -0.014(2)
O6 0.0483(19) 0.135(3) 0.083(3) 0.001(3) 0.012(2) -0.024(2)
O7 0.068(2) 0.076(2) 0.058(2) 0.0108(18) -0.0120(18) -0.0046(17)
O8 0.114(3) 0.103(3) 0.093(3) 0.019(2) 0.002(3) -0.070(3)
O9 0.137(4) 0.082(3) 0.109(4) -0.044(3) 0.024(3) -0.046(3)
O10 0.123(4) 0.210(6) 0.055(2) -0.031(3) -0.025(3) -0.060(4)
C4 0.0245(19) 0.062(3) 0.053(2) 0.008(2) -0.0046(19) -0.0013(18)
C5 0.0296(18) 0.041(2) 0.046(2) -0.0009(19) -0.0017(17) 0.0027(16)
N10 0.034(2) 0.134(4) 0.076(3) 0.050(3) -0.006(2) -0.005(3)
N11 0.045(3) 0.080(3) 0.062(3) 0.023(2) -0.001(2) 0.008(2)
N12 0.0191(15) 0.060(2) 0.0377(17) 0.0020(16) -0.0045(14) 0.0002(15)
N13 0.0273(17) 0.054(2) 0.079(3) 0.022(2) -0.0024(16) -0.0068(15)
N14 0.0221(18) 0.078(3) 0.081(3) 0.033(2) -0.0100(18) -0.0048(17)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.452(5) . ?
C1 N7 1.353(4) . ?
C1 N9 1.298(4) . ?
C2 N3 1.356(5) . ?
C2 N7 1.325(4) . ?
C2 N8 1.378(5) . ?
C3 N4 1.542(6) . ?
C3 N5 1.544(6) . ?
C3 N6 1.537(6) . ?
C3 N8 1.409(5) . ?
N1 O1 1.213(4) . ?
N1 O2 1.207(4) . ?
N2 N3 1.311(4) . ?
N2 O3 1.240(4) . ?
N2 O4 1.259(4) . ?
N4 O7 1.197(5) . ?
N4 O8 1.218(5) . ?
N5 O5 1.216(5) . ?
N5 O6 1.198(5) . ?
N6 O9 1.203(7) . ?
N6 O10 1.187(7) . ?
N8 N9 1.373(4) . ?
C4 N10 1.317(6) . ?
C4 N12 1.335(5) . ?
C4 N14 1.313(5) . ?
C5 N11 1.340(5) . ?
C5 N12 1.365(5) . ?
C5 N13 1.300(5) . ?
N10 H10A 0.82(6) . ?
N10 H10B 0.96(7) . ?
N11 H11A 0.81(5) . ?
N11 H11B 0.83(4) . ?
N12 H12 0.85(6) . ?
N13 N14 1.392(5) . ?
N14 H14 0.88(5) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N7 C1 N1 121.8(3) . . ?
N9 C1 N1 118.9(3) . . ?
N9 C1 N7 119.3(3) . . ?
N3 C2 N8 116.7(3) . . ?
N7 C2 N3 134.9(3) . . ?
N7 C2 N8 107.9(3) . . ?
N4 C3 N5 108.9(3) . . ?
N6 C3 N4 105.9(3) . . ?
N6 C3 N5 109.0(4) . . ?
N8 C3 N4 113.4(3) . . ?
N8 C3 N5 110.2(3) . . ?
N8 C3 N6 109.3(3) . . ?
O1 N1 C1 118.3(4) . . ?
O2 N1 C1 117.2(3) . . ?
O2 N1 O1 124.5(3) . . ?
O3 N2 N3 124.4(3) . . ?
O3 N2 O4 119.9(3) . . ?
O4 N2 N3 115.7(3) . . ?
N2 N3 C2 116.4(3) . . ?
O7 N4 C3 116.6(3) . . ?
O7 N4 O8 129.3(4) . . ?
O8 N4 C3 114.0(4) . . ?
O5 N5 C3 114.2(4) . . ?
O6 N5 C3 118.0(4) . . ?
O6 N5 O5 127.9(5) . . ?
O9 N6 C3 114.5(5) . . ?
O10 N6 C3 116.4(6) . . ?
O10 N6 O9 129.1(6) . . ?
C2 N7 C1 102.1(3) . . ?
C2 N8 C3 128.7(3) . . ?
N9 N8 C2 111.5(3) . . ?
N9 N8 C3 119.8(3) . . ?
C1 N9 N8 99.1(3) . . ?
N10 C4 N12 125.2(4) . . ?
N14 C4 N10 128.7(4) . . ?
N14 C4 N12 106.1(4) . . ?
N11 C5 N12 122.2(4) . . ?
N13 C5 N11 126.3(4) . . ?
N13 C5 N12 111.5(3) . . ?
C4 N10 H10A 113(5) . . ?
C4 N10 H10B 121(4) . . ?
H10A N10 H10B 126(6) . . ?
C5 N11 H11A 119(4) . . ?
C5 N11 H11B 118(3) . . ?
H11A N11 H11B 123(5) . . ?
C4 N12 C5 107.4(3) . . ?
C4 N12 H12 121(4) . . ?
C5 N12 H12 131(4) . . ?
C5 N13 N14 103.0(3) . . ?
C4 N14 N13 111.9(3) . . ?
C4 N14 H14 128(4) . . ?
N13 N14 H14 120(4) . . ?
_shelx_res_file
;
a.res created by SHELXL-2014/7
TITL a_a.res in Pca2(1)
REM Old TITL a in Pca21 #29
REM SHELXT solution in Pca2(1)
REM R1 0.178, Rweak 0.036, Alpha 0.005, Orientation as input
REM Flack x = -0.068 ( 0.636 ) from Parsons' quotients
REM Formula found by SHELXT: C19 N3 O7
CELL 0.71073 9.2722 13.486 12.5676 90 90 90
ZERR 4 0.0011 0.0016 0.0015 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,-Y,+Z
SYMM 0.5-X,+Y,0.5+Z
SFAC C H N O
UNIT 20 24 56 40
ISOR 0.01 0.02 N10
L.S. 10
PLAN 20
TEMP 23
BOND $H
LIST 6
fmap 2
ACTA
TWIN -1 0 0 0 -1 0 0 0 -1 2
OMIT 0 1 0
OMIT 0 4 14
OMIT 11 4 5
OMIT 8 1 -10
REM
REM
REM
WGHT 0.042000
BASF 1.99877
FVAR 0.62804
C1 1 -0.585049 -0.777359 -0.585612 11.00000 0.03260 0.03549 =
0.03631 0.00339 0.00395 0.00002
C2 1 -0.737915 -0.749720 -0.467770 11.00000 0.02813 0.04149 =
0.03564 -0.00121 -0.00505 -0.00938
C3 1 -0.904853 -0.885552 -0.527245 11.00000 0.04807 0.06146 =
0.03458 -0.00677 -0.00045 -0.02511
N1 3 -0.455805 -0.767296 -0.649922 11.00000 0.03549 0.04349 =
0.04530 0.00759 0.00460 0.00433
N2 3 -0.788226 -0.660441 -0.319502 11.00000 0.02977 0.04673 =
0.03610 0.00023 0.00111 -0.00223
N3 3 -0.836898 -0.716643 -0.396673 11.00000 0.02722 0.05447 =
0.03800 -0.01114 -0.00019 -0.00837
N4 3 -0.905492 -0.955935 -0.430549 11.00000 0.06312 0.06375 =
0.05547 0.00626 0.00679 -0.02098
N5 3 -1.040852 -0.819606 -0.523017 11.00000 0.04636 0.09567 =
0.04864 0.00402 -0.01125 -0.02486
N6 3 -0.913240 -0.952620 -0.625911 11.00000 0.08280 0.09218 =
0.05820 -0.02172 0.00705 -0.04960
N7 3 -0.609361 -0.718970 -0.499887 11.00000 0.02591 0.03987 =
0.04059 -0.00231 0.00074 -0.00423
N8 3 -0.780099 -0.826243 -0.533488 11.00000 0.03884 0.05481 =
0.03512 -0.00624 0.00425 -0.02061
N9 3 -0.680508 -0.843250 -0.612270 11.00000 0.04548 0.04703 =
0.03297 -0.00112 0.00513 -0.01059
O1 4 -0.450793 -0.810554 -0.734458 11.00000 0.05907 0.05965 =
0.04334 -0.00562 0.01050 0.00655
O2 4 -0.360791 -0.715161 -0.615464 11.00000 0.04007 0.09826 =
0.07546 -0.02413 0.01721 -0.02313
O3 4 -0.658754 -0.649398 -0.297901 11.00000 0.02894 0.11886 =
0.06383 -0.03937 -0.01278 -0.00004
O4 4 -0.882863 -0.617772 -0.264170 11.00000 0.03709 0.05288 =
0.04479 -0.00694 0.00170 0.00187
O5 4 -1.036132 -0.747707 -0.581296 11.00000 0.06600 0.10905 =
0.08052 0.02843 -0.02620 -0.01385
O6 4 -1.137051 -0.844213 -0.465077 11.00000 0.04830 0.13451 =
0.08301 0.00115 0.01247 -0.02359
O7 4 -0.816394 -0.940982 -0.363517 11.00000 0.06829 0.07596 =
0.05839 0.01077 -0.01202 -0.00457
O8 4 -0.995313 -1.021623 -0.435989 11.00000 0.11448 0.10251 =
0.09328 0.01858 0.00192 -0.06981
O9 4 -0.835154 -1.023767 -0.623021 11.00000 0.13685 0.08228 =
0.10945 -0.04398 0.02438 -0.04552
O10 4 -0.994227 -0.927422 -0.693850 11.00000 0.12282 0.21024 =
0.05517 -0.03109 -0.02482 -0.06002
C4 1 -0.295250 -0.618763 -0.368584 11.00000 0.02448 0.06226 =
0.05287 0.00825 -0.00460 -0.00130
C5 1 -0.283064 -0.523133 -0.507783 11.00000 0.02957 0.04090 =
0.04563 -0.00095 -0.00174 0.00271
N10 3 -0.346147 -0.675011 -0.291537 11.00000 0.03405 0.13450 =
0.07643 0.05025 -0.00623 -0.00536
H10A 2 -0.434439 -0.678551 -0.291940 11.00000 0.09317
H10B 2 -0.282426 -0.711880 -0.245910 11.00000 0.11771
N11 3 -0.329825 -0.471887 -0.592397 11.00000 0.04537 0.08041 =
0.06156 0.02301 -0.00060 0.00789
H11A 2 -0.271350 -0.448680 -0.632775 11.00000 0.06008
H11B 2 -0.417818 -0.461433 -0.597450 11.00000 0.04818
N12 3 -0.375294 -0.571378 -0.440793 11.00000 0.01905 0.06046 =
0.03769 0.00200 -0.00450 0.00021
H12 2 -0.465859 -0.580059 -0.444264 11.00000 0.09721
N13 3 -0.149484 -0.535116 -0.479045 11.00000 0.02727 0.05444 =
0.07890 0.02151 -0.00237 -0.00681
N14 3 -0.160571 -0.596946 -0.390732 11.00000 0.02209 0.07826 =
0.08132 0.03325 -0.00997 -0.00475
H14 2 -0.082779 -0.613900 -0.355468 11.00000 0.08324
HKLF 4
REM a_a.res in Pca2(1)
REM R1 = 0.0432 for 2425 Fo > 4sig(Fo) and 0.0726 for all 3474 data
REM 287 parameters refined using 7 restraints
END
WGHT 0.0420 0.0000
REM Highest difference peak 0.157, deepest hole -0.193, 1-sigma level 0.037
Q1 1 -0.8046 -1.0346 -0.6232 11.00000 0.05 0.16
Q2 1 -0.9563 -0.9013 -0.6498 11.00000 0.05 0.15
Q3 1 -0.4269 -0.5387 -0.2764 11.00000 0.05 0.14
Q4 1 -0.8828 -0.9635 -0.6222 11.00000 0.05 0.14
Q5 1 -0.6993 -0.6955 -0.2769 11.00000 0.05 0.13
Q6 1 -0.6034 -0.7405 -0.2646 11.00000 0.05 0.13
Q7 1 -1.0219 -0.8633 -0.7140 11.00000 0.05 0.13
Q8 1 -1.0712 -0.8746 -0.7060 11.00000 0.05 0.13
Q9 1 -1.1578 -0.8516 -0.6663 11.00000 0.05 0.13
Q10 1 -0.9514 -0.9396 -0.7061 11.00000 0.05 0.12
Q11 1 -1.1526 -0.8847 -0.8262 11.00000 0.05 0.12
Q12 1 -1.1261 -0.9026 -0.4136 11.00000 0.05 0.12
Q13 1 -0.8345 -0.7997 -0.5552 11.00000 0.05 0.12
Q14 1 -0.3473 -0.7363 -0.3370 11.00000 0.05 0.12
Q15 1 -0.4072 -0.5018 -0.6964 11.00000 0.05 0.12
Q16 1 -0.8353 -0.8577 -0.5213 11.00000 0.05 0.11
Q17 1 -0.7556 -0.8348 -0.3361 11.00000 0.05 0.11
Q18 1 -0.4337 -0.6798 -0.6323 11.00000 0.05 0.11
Q19 1 -0.8203 -0.7386 -0.6180 11.00000 0.05 0.11
Q20 1 -0.4914 -0.7370 -0.7905 11.00000 0.05 0.11
;
_shelx_res_checksum 97779
_shelx_SHELXL_version_number 2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -1(2)
2 2(2)
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_mo_2016281_0m
_database_code_depnum_ccdc_archive 'CCDC 1506809'
_audit_update_record
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date 2017-07-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C3 N9 O10, H2 O, H5 N2'
_chemical_formula_sum 'C3 H7 N11 O11'
_chemical_formula_weight 373.20
_chemical_absolute_configuration .
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 8.2280(4)
_cell_length_b 7.3357(3)
_cell_length_c 11.3167(5)
_cell_angle_alpha 90
_cell_angle_beta 94.923(3)
_cell_angle_gamma 90
_cell_volume 680.54(5)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2730
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 27.39
_cell_measurement_theta_min 2.48
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.180
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.6812
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0505 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.9136.
The \l/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear whiteish colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier whiteish
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.821
_exptl_crystal_density_meas .
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 380
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.2
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0753
_diffrn_reflns_av_unetI/netI 0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 6258
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.465
_diffrn_reflns_theta_min 1.806
_diffrn_ambient_temperature 296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.821
_reflns_Friedel_fraction_full 0.980
_reflns_Friedel_fraction_max 0.960
_reflns_number_gt 2575
_reflns_number_total 3060
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection ?
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.181
_refine_diff_density_min -0.223
_refine_diff_density_rms 0.052
_refine_ls_abs_structure_details
;
Flack x determined using 957 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.0(7)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.956
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 244
_refine_ls_number_reflns 3060
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0505
_refine_ls_R_factor_gt 0.0369
_refine_ls_restrained_S_all 0.956
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0419P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0735
_refine_ls_wR_factor_ref 0.0776
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.5 times of:
All N(H,H) groups, All N(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
O1W(H1WA,H1WB)
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_special_details
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual = -1, Ralpha = 0.063
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1718(3) 0.2560(4) 0.5112(2) 0.0719(7) Uani 1 1 d . . . . .
O1W O 1.0390(2) 1.0594(3) 0.80338(18) 0.0515(5) Uani 1 1 d . . . . .
H1WA H 1.1049 1.0637 0.7496 0.077 Uiso 1 1 d G . . . .
H1WB H 0.9484 1.0155 0.7747 0.077 Uiso 1 1 d G . . . .
O2 O 0.0222(3) 0.4166(4) 0.6211(3) 0.0796(8) Uani 1 1 d . . . . .
O3 O 0.5008(3) 0.4988(4) 0.48172(19) 0.0636(7) Uani 1 1 d . . . . .
O4 O 0.2750(4) 0.6410(3) 0.43071(18) 0.0704(8) Uani 1 1 d . . . A 2
O5 O 0.3992(3) -0.0574(3) 0.8812(2) 0.0574(6) Uani 1 1 d . . . . .
O6 O 0.6186(3) 0.0526(3) 0.97226(18) 0.0505(5) Uani 1 1 d . . . . .
O7 O 0.2106(3) 0.8058(3) 0.62512(19) 0.0600(6) Uani 1 1 d . . . . .
O8 O 0.2161(3) 0.6385(3) 0.78236(17) 0.0549(6) Uani 1 1 d . . . . .
O9 O 0.7382(3) 0.8795(3) 0.7478(2) 0.0581(6) Uani 1 1 d . . . B 1
O10 O 0.7972(3) 0.6439(3) 0.8548(2) 0.0790(9) Uani 1 1 d . . . . .
N1 N 0.1472(3) 0.3783(3) 0.5780(2) 0.0466(6) Uani 1 1 d . . . . .
N2 N 0.3671(3) 0.5518(3) 0.49702(18) 0.0429(6) Uani 1 1 d . . . . .
N3 N 0.2341(3) 0.6674(3) 0.67893(19) 0.0375(5) Uani 1 1 d . . . . .
N4 N 0.4080(3) 0.3992(3) 0.69161(18) 0.0336(5) Uani 1 1 d . . . . .
N5 N 0.3686(3) 0.2356(3) 0.74094(18) 0.0327(5) Uani 1 1 d . . . . .
N6 N 0.5043(3) 0.0578(3) 0.89601(19) 0.0367(5) Uani 1 1 d . . . . .
N7 N 0.6088(3) 0.3485(3) 0.82933(17) 0.0307(5) Uani 1 1 d . . . . .
N8 N 0.5876(3) 0.6386(3) 0.71557(19) 0.0387(5) Uani 1 1 d . . . . .
N9 N 0.7132(3) 0.7194(3) 0.7753(2) 0.0412(6) Uani 1 1 d . . . . .
C1 C 0.2967(3) 0.4968(4) 0.6146(2) 0.0321(6) Uani 1 1 d . . . . .
C2 C 0.5502(3) 0.4698(4) 0.7493(2) 0.0305(5) Uani 1 1 d . . . . .
C3 C 0.4932(3) 0.2169(3) 0.8189(2) 0.0298(5) Uani 1 1 d . . . . .
N10 N 1.0918(3) 0.8173(3) 1.0019(2) 0.0360(5) Uani 1 1 d . . . . .
H10A H 1.082(4) 0.694(5) 0.991(3) 0.054 Uiso 1 1 d R . . . .
H10B H 1.108(4) 0.870(5) 0.929(3) 0.054 Uiso 1 1 d R . . . .
H10C H 1.182(4) 0.848(4) 1.056(3) 0.054 Uiso 1 1 d R . . . .
N11 N 0.9495(3) 0.9038(4) 1.0425(2) 0.0424(6) Uani 1 1 d . . . . .
H11A H 0.953(5) 0.871(5) 1.116(4) 0.064 Uiso 1 1 d R . . . .
H11B H 0.868(5) 0.855(5) 1.003(3) 0.064 Uiso 1 1 d R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0817(18) 0.0544(15) 0.0755(15) -0.0248(13) -0.0175(14) -0.0172(13)
O1W 0.0418(13) 0.0571(13) 0.0551(11) -0.0036(11) 0.0017(10) -0.0077(11)
O2 0.0382(14) 0.085(2) 0.114(2) -0.0107(17) -0.0061(15) -0.0144(13)
O3 0.0534(14) 0.0930(19) 0.0456(11) -0.0036(12) 0.0115(11) -0.0033(14)
O4 0.118(2) 0.0563(14) 0.0351(10) 0.0079(11) -0.0047(12) 0.0281(15)
O5 0.0504(13) 0.0489(14) 0.0702(14) 0.0182(11) -0.0107(11) -0.0209(11)
O6 0.0459(12) 0.0477(12) 0.0544(11) 0.0165(11) -0.0155(10) -0.0035(10)
O7 0.0837(17) 0.0437(13) 0.0520(12) 0.0031(11) 0.0025(12) 0.0209(12)
O8 0.0685(15) 0.0606(14) 0.0374(10) -0.0029(10) 0.0142(10) -0.0023(12)
O9 0.0582(14) 0.0402(12) 0.0725(14) 0.0124(11) -0.0148(12) -0.0203(10)
O10 0.0776(19) 0.0471(14) 0.1003(19) 0.0206(14) -0.0615(16) -0.0202(13)
N1 0.0398(15) 0.0423(15) 0.0536(14) 0.0042(12) -0.0194(12) -0.0060(11)
N2 0.0588(16) 0.0398(12) 0.0291(10) -0.0043(10) -0.0015(11) -0.0023(12)
N3 0.0343(12) 0.0415(14) 0.0360(11) -0.0022(10) -0.0006(9) -0.0016(10)
N4 0.0318(11) 0.0320(11) 0.0348(10) 0.0039(9) -0.0089(9) -0.0053(9)
N5 0.0308(11) 0.0306(11) 0.0357(10) 0.0021(9) -0.0030(9) -0.0048(9)
N6 0.0353(12) 0.0338(12) 0.0403(11) 0.0051(10) -0.0015(10) -0.0022(10)
N7 0.0274(10) 0.0312(11) 0.0326(10) 0.0017(9) -0.0029(8) -0.0025(9)
N8 0.0361(13) 0.0354(12) 0.0420(11) 0.0077(10) -0.0110(10) -0.0111(10)
N9 0.0383(13) 0.0334(12) 0.0495(13) 0.0022(10) -0.0105(11) -0.0073(11)
C1 0.0306(13) 0.0317(13) 0.0324(11) 0.0009(10) -0.0068(10) -0.0023(10)
C2 0.0250(12) 0.0365(14) 0.0290(11) -0.0025(10) -0.0027(9) -0.0047(10)
C3 0.0281(13) 0.0299(12) 0.0308(11) 0.0017(10) -0.0003(10) -0.0023(10)
N10 0.0305(12) 0.0327(12) 0.0439(12) -0.0047(10) -0.0019(10) -0.0003(10)
N11 0.0330(13) 0.0449(14) 0.0492(13) -0.0030(12) 0.0028(11) 0.0032(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.201(4) . ?
O2 N1 1.208(4) . ?
O3 N2 1.194(4) . ?
O4 N2 1.211(3) . ?
O5 N6 1.210(3) . ?
O6 N6 1.221(3) . ?
O7 N3 1.191(3) . ?
O8 N3 1.211(3) . ?
O9 N9 1.237(3) . ?
O10 N9 1.220(3) . ?
N1 C1 1.535(3) . ?
N2 C1 1.550(3) . ?
N3 C1 1.558(3) . ?
N4 N5 1.374(3) . ?
N4 C1 1.405(3) . ?
N4 C2 1.390(3) . ?
N5 C3 1.302(3) . ?
N6 C3 1.455(3) . ?
N7 C2 1.331(3) . ?
N7 C3 1.353(3) . ?
N8 N9 1.326(3) . ?
N8 C2 1.339(3) . ?
N10 N11 1.441(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 128.5(3) . . ?
O1 N1 C1 114.7(3) . . ?
O2 N1 C1 116.7(3) . . ?
O3 N2 O4 128.4(3) . . ?
O3 N2 C1 117.2(2) . . ?
O4 N2 C1 114.4(2) . . ?
O7 N3 O8 128.0(3) . . ?
O7 N3 C1 119.5(2) . . ?
O8 N3 C1 112.6(2) . . ?
N5 N4 C1 122.2(2) . . ?
N5 N4 C2 110.69(19) . . ?
C2 N4 C1 125.4(2) . . ?
C3 N5 N4 99.7(2) . . ?
O5 N6 O6 125.0(2) . . ?
O5 N6 C3 118.0(2) . . ?
O6 N6 C3 116.9(2) . . ?
C2 N7 C3 101.96(19) . . ?
N9 N8 C2 117.2(2) . . ?
O9 N9 N8 115.8(2) . . ?
O10 N9 O9 121.4(2) . . ?
O10 N9 N8 122.7(2) . . ?
N1 C1 N2 105.4(2) . . ?
N1 C1 N3 107.0(2) . . ?
N2 C1 N3 110.8(2) . . ?
N4 C1 N1 110.1(2) . . ?
N4 C1 N2 113.2(2) . . ?
N4 C1 N3 110.12(18) . . ?
N7 C2 N4 108.1(2) . . ?
N7 C2 N8 137.2(2) . . ?
N8 C2 N4 114.6(2) . . ?
N5 C3 N6 119.8(2) . . ?
N5 C3 N7 119.4(2) . . ?
N7 C3 N6 120.9(2) . . ?
_shelx_res_file
;
mo_2016281_0m.res created by SHELXL-2014/7
TITL mo_2016281_0m_a.res in P2(1)
REM Old TITL mo_2016281_0m in P21 #4
REM SHELXT solution in P2(1)
REM R1 0.157, Rweak 0.043, Alpha 0.004, Orientation as input
REM Flack x = -0.205 ( 0.423 ) from Parsons' quotients
REM Formula found by SHELXT: C17 N O7
CELL 0.71073 8.228 7.3357 11.3167 90 94.923 90
ZERR 2 0.0004 0.0003 0.0005 0 0.003 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 6 14 22 22
L.S. 20
PLAN -40 0 0
TEMP 23
fmap 2
acta
OMIT -4 -1 7
OMIT -4 0 6
OMIT 6 -1 1
OMIT -4 2 5
REM
REM
REM
WGHT 0.041900
FVAR 0.85100
O1 4 0.171800 0.256008 0.511167 11.00000 0.08172 0.05439 =
0.07550 -0.02480 -0.01754 -0.01719
AFIX 6
O1W 4 1.038979 1.059423 0.803378 11.00000 0.04175 0.05713 =
0.05514 -0.00358 0.00175 -0.00772
H1WA 2 1.104908 1.063748 0.749637 11.00000 -1.50000
H1WB 2 0.948409 1.015489 0.774720 11.00000 -1.50000
AFIX 0
O2 4 0.022191 0.416567 0.621056 11.00000 0.03818 0.08480 =
0.11378 -0.01069 -0.00606 -0.01442
O3 4 0.500845 0.498786 0.481716 11.00000 0.05337 0.09302 =
0.04561 -0.00362 0.01154 -0.00333
PART 2
O4 4 0.275042 0.641022 0.430708 11.00000 0.11799 0.05632 =
0.03509 0.00790 -0.00474 0.02813
PART 0
O5 4 0.399157 -0.057376 0.881224 11.00000 0.05036 0.04890 =
0.07025 0.01816 -0.01075 -0.02089
O6 4 0.618611 0.052610 0.972262 11.00000 0.04591 0.04769 =
0.05437 0.01647 -0.01549 -0.00352
O7 4 0.210624 0.805784 0.625123 11.00000 0.08370 0.04370 =
0.05197 0.00312 0.00253 0.02091
O8 4 0.216095 0.638545 0.782362 11.00000 0.06854 0.06056 =
0.03737 -0.00289 0.01420 -0.00228
PART 1
O9 4 0.738154 0.879531 0.747816 11.00000 0.05817 0.04017 =
0.07251 0.01245 -0.01478 -0.02026
PART 0
O10 4 0.797183 0.643871 0.854850 11.00000 0.07760 0.04712 =
0.10030 0.02061 -0.06148 -0.02021
N1 3 0.147173 0.378287 0.577967 11.00000 0.03981 0.04230 =
0.05363 0.00425 -0.01940 -0.00605
N2 3 0.367098 0.551838 0.497024 11.00000 0.05882 0.03982 =
0.02913 -0.00432 -0.00151 -0.00226
N3 3 0.234149 0.667441 0.678933 11.00000 0.03429 0.04152 =
0.03604 -0.00219 -0.00060 -0.00157
N4 3 0.407997 0.399192 0.691609 11.00000 0.03176 0.03202 =
0.03483 0.00391 -0.00893 -0.00534
N5 3 0.368603 0.235632 0.740942 11.00000 0.03076 0.03062 =
0.03567 0.00206 -0.00303 -0.00482
N6 3 0.504288 0.057762 0.896010 11.00000 0.03529 0.03378 =
0.04031 0.00511 -0.00150 -0.00217
N7 3 0.608778 0.348476 0.829330 11.00000 0.02740 0.03118 =
0.03256 0.00167 -0.00289 -0.00253
N8 3 0.587585 0.638565 0.715568 11.00000 0.03610 0.03544 =
0.04201 0.00770 -0.01096 -0.01111
N9 3 0.713221 0.719417 0.775320 11.00000 0.03826 0.03340 =
0.04948 0.00218 -0.01053 -0.00732
C1 1 0.296742 0.496800 0.614630 11.00000 0.03065 0.03169 =
0.03239 0.00088 -0.00677 -0.00230
C2 1 0.550177 0.469821 0.749261 11.00000 0.02502 0.03654 =
0.02901 -0.00248 -0.00265 -0.00471
C3 1 0.493239 0.216879 0.818931 11.00000 0.02805 0.02993 =
0.03083 0.00168 -0.00028 -0.00228
N10 3 1.091781 0.817311 1.001869 11.00000 0.03055 0.03268 =
0.04388 -0.00468 -0.00188 -0.00027
H10A 2 1.082308 0.693606 0.990880 11.00000 -1.50000
H10B 2 1.107833 0.870424 0.928545 11.00000 -1.50000
H10C 2 1.182328 0.848381 1.055911 11.00000 -1.50000
N11 3 0.949468 0.903751 1.042483 11.00000 0.03295 0.04486 =
0.04921 -0.00297 0.00283 0.00324
H11A 2 0.952836 0.870939 1.116349 11.00000 -1.50000
H11B 2 0.867659 0.854812 1.003067 11.00000 -1.50000
HKLF 4
REM mo_2016281_0m_a.res in P2(1)
REM R1 = 0.0369 for 2575 Fo > 4sig(Fo) and 0.0505 for all 3060 data
REM 244 parameters refined using 1 restraints
END
WGHT 0.0419 0.0000
REM Highest difference peak 0.181, deepest hole -0.223, 1-sigma level 0.052
Q1 1 0.0365 0.1972 0.7832 11.00000 0.05 0.18
Q2 1 -0.1908 0.8109 0.7081 11.00000 0.05 0.17
Q3 1 0.2496 0.3133 0.8776 11.00000 0.05 0.15
Q4 1 0.2364 -0.0100 0.8370 11.00000 0.05 0.15
Q5 1 -0.1953 1.0557 0.5522 11.00000 0.05 0.15
Q6 1 -0.0625 0.2189 0.6583 11.00000 0.05 0.14
Q7 1 -0.3476 0.8129 0.5217 11.00000 0.05 0.14
Q8 1 -0.1008 0.9504 0.6479 11.00000 0.05 0.14
Q9 1 0.7955 0.2801 0.1262 11.00000 0.05 0.14
Q10 1 -0.0439 0.6196 0.6982 11.00000 0.05 0.13
Q11 1 -0.0910 0.2547 0.7522 11.00000 0.05 0.13
Q12 1 0.2321 -0.0032 1.0187 11.00000 0.05 0.13
Q13 1 0.3544 0.4620 0.9020 11.00000 0.05 0.13
Q14 1 0.0138 0.6803 0.7854 11.00000 0.05 0.13
Q15 1 -0.0626 0.3690 0.7120 11.00000 0.05 0.13
Q16 1 -0.0700 0.6863 0.6994 11.00000 0.05 0.13
Q17 1 0.2003 0.4919 0.8178 11.00000 0.05 0.12
Q18 1 -0.0745 0.5741 0.6630 11.00000 0.05 0.12
Q19 1 0.3968 0.2583 0.8168 11.00000 0.05 0.12
Q20 1 0.4996 0.3133 1.0410 11.00000 0.05 0.12
Q21 1 -0.3307 0.2849 0.5264 11.00000 0.05 0.12
Q22 1 -0.3682 0.8488 0.6000 11.00000 0.05 0.12
Q23 1 0.3358 0.0434 0.9161 11.00000 0.05 0.12
Q24 1 -0.0075 0.4060 0.7727 11.00000 0.05 0.12
Q25 1 -0.0843 0.4003 0.6259 11.00000 0.05 0.12
Q26 1 -0.3679 0.6961 0.5168 11.00000 0.05 0.12
Q27 1 0.0928 0.3211 0.7873 11.00000 0.05 0.12
Q28 1 0.3628 -0.0551 1.0383 11.00000 0.05 0.12
Q29 1 -0.0218 0.8525 0.6904 11.00000 0.05 0.11
Q30 1 0.4682 0.2391 0.9531 11.00000 0.05 0.11
Q31 1 -0.1507 0.9006 0.7212 11.00000 0.05 0.11
Q32 1 0.3006 0.2214 0.9578 11.00000 0.05 0.11
Q33 1 0.1730 0.2432 0.7816 11.00000 0.05 0.11
Q34 1 -0.2948 1.0189 0.5590 11.00000 0.05 0.11
Q35 1 0.1650 -0.0123 0.7825 11.00000 0.05 0.11
Q36 1 -0.2361 0.2474 0.6056 11.00000 0.05 0.11
Q37 1 -0.2826 1.1250 0.6408 11.00000 0.05 0.11
Q38 1 0.1184 0.7366 0.6234 11.00000 0.05 0.11
Q39 1 0.5977 0.2281 1.0403 11.00000 0.05 0.11
Q40 1 0.1943 0.2256 0.8872 11.00000 0.05 0.11
;
_shelx_res_checksum 85282
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_mo_2016291_0m
_database_code_depnum_ccdc_archive 'CCDC 1506810'
_audit_update_record
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date 2017-07-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C3 N9 O10, H4 N O, H2 O'
_chemical_formula_sum 'C3 H6 N10 O12'
_chemical_formula_weight 374.18
_chemical_absolute_configuration .
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 7.8388(15)
_cell_length_b 7.8730(15)
_cell_length_c 10.987(2)
_cell_angle_alpha 90
_cell_angle_beta 90.413(11)
_cell_angle_gamma 90
_cell_volume 678.1(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2049
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 25.381
_cell_measurement_theta_min 2.599
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.184
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.5205
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1021 before and 0.0718 after correction. The Ratio of minimum to maximum transmission is 0.6981. The \l/2 correction factor is 0.0015.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.833
_exptl_crystal_density_meas .
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 380
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.08
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0417
_diffrn_reflns_av_unetI/netI 0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 4230
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 28.205
_diffrn_reflns_theta_min 1.854
_diffrn_ambient_temperature 296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.866
_reflns_Friedel_fraction_full 0.997
_reflns_Friedel_fraction_max 0.988
_reflns_number_gt 2034
_reflns_number_total 2832
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection ?
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.219
_refine_diff_density_min -0.227
_refine_diff_density_rms 0.046
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack 0(2)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.006
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 258
_refine_ls_number_reflns 2832
_refine_ls_number_restraints 71
_refine_ls_R_factor_all 0.0669
_refine_ls_R_factor_gt 0.0426
_refine_ls_restrained_S_all 1.004
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0524P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1068
_refine_ls_wR_factor_ref 0.1210
_refine_special_details
;
Refined as a 2-component inversion twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 1(2)
0(2)
2. Fixed Uiso
At 1.5 times of:
All N(H,H) groups, All O(H) groups, All O(H,H) groups
3. Restrained distances
O11A-N10
1.42 with sigma of 0.02
4. Rigid bond restraints
All non-hydrogen atoms
with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(O1W) \\sim Ueq, Uanis(O1WA) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
6. Others
Sof(O1WA)=Sof(H1WC)=Sof(H1WD)=1-FVAR(1)
Sof(O1W)=Sof(H1WA)=Sof(H1WB)=FVAR(1)
Fixed Sof: O11(0.5) H11(0.5) O11A(0.5) H11A(0.5)
7.a Free rotating group:
O1W(H1WA,H1WB), O1WA(H1WC,H1WD)
7.b Rotating group:
N10(H10A,H10B)
7.c Tetrahedral OH refined with riding coordinates:
O11A(H11A)
7.d Idealised tetrahedral OH refined as rotating group:
O11(H11)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
_atom_sites_special_details
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual = -1, Ralpha = 0.078
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 1.3931(3) 1.1807(4) 1.1691(3) 0.0386(7) Uani 1 1 d . U . . .
N2 N 1.6407(4) 1.0790(4) 1.2565(3) 0.0396(7) Uani 1 1 d . U . . .
N7 N 1.7754(4) 1.4938(5) 1.3157(3) 0.0486(8) Uani 1 1 d . U . . .
O1 O 1.6058(4) 0.7889(5) 1.1287(3) 0.0662(9) Uani 1 1 d . U . . .
O2 O 1.3803(4) 0.8907(5) 1.0363(3) 0.0632(9) Uani 1 1 d . U . . .
N4 N 1.6017(4) 1.2381(5) 1.3008(3) 0.0413(7) Uani 1 1 d . U . . .
O4 O 1.2442(5) 1.6792(5) 1.2513(4) 0.0742(10) Uani 1 1 d . U . . .
N6 N 1.6273(5) 1.3725(5) 1.5037(3) 0.0518(9) Uani 1 1 d . U . . .
O5 O 1.7940(4) 1.4772(5) 1.2075(3) 0.0656(9) Uani 1 1 d . U . . .
N8 N 1.4084(4) 1.4579(5) 1.2797(3) 0.0465(8) Uani 1 1 d . U . . .
N1 N 1.4984(4) 0.8996(5) 1.1109(3) 0.0470(8) Uani 1 1 d . U . . .
N9 N 1.2830(4) 1.5325(5) 1.2161(3) 0.0522(9) Uani 1 1 d . U . . .
O3 O 1.2126(5) 1.4684(5) 1.1274(4) 0.0878(14) Uani 1 1 d . U . . .
O8 O 1.7171(5) 1.4520(5) 1.5739(3) 0.0811(11) Uani 1 1 d . U . . .
O9 O 1.8447(5) 1.1035(5) 1.4788(3) 0.0774(11) Uani 1 1 d . U . . .
N10 N 1.0881(4) 2.1393(5) 1.0212(4) 0.0523(9) Uani 1 1 d D U . . .
H10A H 1.1687 2.1716 1.0701 0.078 Uiso 1 1 d GR . . B .
H10B H 1.1370 2.1460 0.9417 0.078 Uiso 1 1 d GR . . . .
O6 O 1.7994(5) 1.6208(5) 1.3761(3) 0.0771(11) Uani 1 1 d . U . . .
N5 N 1.8717(4) 1.2231(5) 1.4119(3) 0.0542(9) Uani 1 1 d . U . . .
O7 O 1.4876(5) 1.3189(6) 1.5206(3) 0.0793(12) Uani 1 1 d . U . . .
C2 C 1.4521(4) 1.2999(5) 1.2450(3) 0.0382(8) Uani 1 1 d . U . . .
O10 O 2.0054(4) 1.2682(6) 1.3674(4) 0.0910(13) Uani 1 1 d . U . . .
C1 C 1.5112(4) 1.0558(5) 1.1820(3) 0.0369(8) Uani 1 1 d . U . . .
C3 C 1.7112(4) 1.3289(5) 1.3798(3) 0.0422(9) Uani 1 1 d . U . . .
O1W O 0.9735(8) 1.8793(12) 1.1787(12) 0.070(3) Uani 0.67(3) 1 d . U P A 1
H1WA H 1.0598 1.8278 1.2080 0.105 Uiso 0.67(3) 1 d G . P A 1
H1WB H 0.9046 1.9029 1.2356 0.105 Uiso 0.67(3) 1 d G . P A 1
O11 O 0.9383(12) 2.2366(12) 1.0144(11) 0.080(3) Uani 0.5 1 d . U P B 1
H11 H 0.8706 2.1912 0.9673 0.120 Uiso 0.5 1 calc GR . P B 1
O11A O 0.9495(12) 2.1793(17) 1.0824(11) 0.098(4) Uani 0.5 1 d D U P B 2
H11A H 0.9335 2.2821 1.0783 0.147 Uiso 0.5 1 calc R . P B 2
H10C H 1.037(11) 2.060(13) 1.077(8) 0.13(3) Uiso 1 1 d . . . . .
O1WA O 0.988(3) 1.929(3) 1.248(3) 0.099(7) Uani 0.33(3) 1 d . U P A 2
H1WC H 0.9491 1.9946 1.3032 0.149 Uiso 0.33(3) 1 d G . P A 2
H1WD H 1.0760 1.8782 1.2753 0.149 Uiso 0.33(3) 1 d G . P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N3 0.0368(14) 0.0434(19) 0.0355(15) 0.0010(13) -0.0010(12) 0.0032(13)
N2 0.0376(14) 0.043(2) 0.0379(15) 0.0064(14) 0.0016(12) 0.0045(13)
N7 0.0457(17) 0.054(2) 0.0457(18) 0.0054(17) -0.0032(14) -0.0031(15)
O1 0.0753(19) 0.050(2) 0.073(2) -0.0090(16) -0.0082(16) 0.0250(17)
O2 0.0661(18) 0.057(2) 0.0664(19) -0.0150(16) -0.0183(15) 0.0051(16)
N4 0.0422(15) 0.042(2) 0.0391(16) -0.0031(13) -0.0075(12) 0.0073(13)
O4 0.079(2) 0.055(2) 0.089(3) -0.0052(19) -0.0060(18) 0.0284(18)
N6 0.064(2) 0.052(2) 0.0388(17) 0.0055(17) -0.0009(16) -0.0001(18)
O5 0.080(2) 0.073(2) 0.0441(16) 0.0090(16) 0.0144(15) 0.0079(18)
N8 0.0432(16) 0.044(2) 0.0518(19) -0.0054(15) -0.0098(14) 0.0123(15)
N1 0.0523(18) 0.043(2) 0.0462(18) -0.0021(15) 0.0004(14) 0.0044(15)
N9 0.0452(17) 0.045(2) 0.066(2) 0.0043(18) -0.0085(16) 0.0081(15)
O3 0.089(2) 0.060(2) 0.113(3) -0.009(2) -0.066(2) 0.020(2)
O8 0.123(3) 0.076(3) 0.0448(17) -0.0108(18) -0.0039(18) -0.021(2)
O9 0.086(2) 0.074(3) 0.072(2) 0.026(2) -0.0226(18) 0.013(2)
N10 0.0405(16) 0.057(3) 0.059(2) -0.0029(18) -0.0020(16) 0.0013(16)
O6 0.100(3) 0.059(2) 0.072(2) -0.0023(19) -0.006(2) -0.0188(19)
N5 0.0470(19) 0.064(3) 0.0516(19) 0.0046(18) -0.0123(15) 0.0076(17)
O7 0.0657(19) 0.117(4) 0.0552(19) 0.002(2) 0.0180(15) -0.004(2)
C2 0.0358(16) 0.041(2) 0.0376(17) 0.0027(16) -0.0031(14) 0.0059(16)
O10 0.0503(18) 0.103(3) 0.119(3) 0.030(3) -0.0059(19) 0.0132(19)
C1 0.0392(17) 0.037(2) 0.0350(17) 0.0044(14) 0.0025(14) 0.0043(15)
C3 0.0425(18) 0.045(2) 0.0385(18) 0.0022(16) -0.0063(15) 0.0002(16)
O1W 0.053(3) 0.068(5) 0.090(7) 0.017(4) -0.010(3) 0.006(3)
O11 0.070(5) 0.057(5) 0.112(7) -0.020(5) -0.051(6) 0.017(4)
O11A 0.065(5) 0.111(9) 0.119(9) -0.048(7) 0.028(6) 0.020(5)
O1WA 0.075(8) 0.102(11) 0.121(13) -0.015(9) 0.005(8) 0.025(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C2 1.336(5) . ?
N3 C1 1.357(5) . ?
N2 N4 1.379(5) . ?
N2 C1 1.312(5) . ?
N7 O5 1.206(4) . ?
N7 O6 1.214(5) . ?
N7 C3 1.561(5) . ?
O1 N1 1.226(4) . ?
O2 N1 1.234(4) . ?
N4 C2 1.406(4) . ?
N4 C3 1.411(5) . ?
O4 N9 1.256(5) . ?
N6 O8 1.214(5) . ?
N6 O7 1.190(5) . ?
N6 C3 1.555(5) . ?
N8 N9 1.338(4) . ?
N8 C2 1.346(5) . ?
N1 C1 1.460(5) . ?
N9 O3 1.225(5) . ?
O9 N5 1.214(5) . ?
N10 H10A 0.8645 . ?
N10 H10B 0.9588 . ?
N10 O11 1.404(9) . ?
N10 O11A 1.320(9) . ?
N10 H10C 0.96(9) . ?
N5 O10 1.213(5) . ?
N5 C3 1.547(5) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?
O11 H11 0.8200 . ?
O11A H11A 0.8200 . ?
O11A H10C 1.16(9) . ?
O1WA H1WC 0.8500 . ?
O1WA H1WD 0.8500 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N3 C1 102.2(3) . . ?
C1 N2 N4 100.1(3) . . ?
O5 N7 O6 127.5(4) . . ?
O5 N7 C3 113.3(4) . . ?
O6 N7 C3 119.1(3) . . ?
N2 N4 C2 110.3(3) . . ?
N2 N4 C3 122.8(3) . . ?
C2 N4 C3 126.5(3) . . ?
O8 N6 C3 115.1(3) . . ?
O7 N6 O8 127.9(4) . . ?
O7 N6 C3 117.0(4) . . ?
N9 N8 C2 116.5(3) . . ?
O1 N1 O2 125.2(4) . . ?
O1 N1 C1 118.0(3) . . ?
O2 N1 C1 116.8(3) . . ?
O4 N9 N8 114.9(4) . . ?
O3 N9 O4 121.0(4) . . ?
O3 N9 N8 124.0(4) . . ?
H10A N10 H10B 104.7 . . ?
H10A N10 H10C 95.6 . . ?
H10B N10 H10C 142.1 . . ?
O11 N10 H10A 118.7 . . ?
O11 N10 H10B 105.1 . . ?
O11 N10 H10C 92(5) . . ?
O11A N10 H10A 102.4 . . ?
O11A N10 H10B 141.9 . . ?
O11A N10 H10C 59(6) . . ?
O9 N5 C3 114.3(4) . . ?
O10 N5 O9 128.7(4) . . ?
O10 N5 C3 117.0(4) . . ?
N3 C2 N4 108.2(3) . . ?
N3 C2 N8 137.6(3) . . ?
N8 C2 N4 114.2(3) . . ?
N3 C1 N1 120.7(3) . . ?
N2 C1 N3 119.2(3) . . ?
N2 C1 N1 120.1(3) . . ?
N4 C3 N7 109.9(3) . . ?
N4 C3 N6 113.0(3) . . ?
N4 C3 N5 110.9(3) . . ?
N6 C3 N7 110.6(3) . . ?
N5 C3 N7 106.7(3) . . ?
N5 C3 N6 105.5(3) . . ?
H1WA O1W H1WB 109.5 . . ?
N10 O11 H11 109.5 . . ?
N10 O11A H11A 109.5 . . ?
N10 O11A H10C 45(5) . . ?
H11A O11A H10C 151.8 . . ?
H1WC O1WA H1WD 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N4 C2 N3 1.9(4) . . . . ?
N2 N4 C2 N8 -177.5(3) . . . . ?
N2 N4 C3 N7 115.3(4) . . . . ?
N2 N4 C3 N6 -120.6(4) . . . . ?
N2 N4 C3 N5 -2.4(5) . . . . ?
O1 N1 C1 N3 -177.9(4) . . . . ?
O1 N1 C1 N2 4.2(5) . . . . ?
O2 N1 C1 N3 2.8(5) . . . . ?
O2 N1 C1 N2 -175.0(4) . . . . ?
N4 N2 C1 N3 1.4(4) . . . . ?
N4 N2 C1 N1 179.3(3) . . . . ?
O5 N7 C3 N4 -33.7(4) . . . . ?
O5 N7 C3 N6 -159.1(3) . . . . ?
O5 N7 C3 N5 86.7(4) . . . . ?
N9 N8 C2 N3 -9.1(7) . . . . ?
N9 N8 C2 N4 170.1(3) . . . . ?
O8 N6 C3 N7 -55.7(4) . . . . ?
O8 N6 C3 N4 -179.4(4) . . . . ?
O8 N6 C3 N5 59.2(5) . . . . ?
O9 N5 C3 N7 169.2(4) . . . . ?
O9 N5 C3 N4 -71.1(4) . . . . ?
O9 N5 C3 N6 51.6(5) . . . . ?
O6 N7 C3 N4 145.8(4) . . . . ?
O6 N7 C3 N6 20.4(5) . . . . ?
O6 N7 C3 N5 -93.9(4) . . . . ?
O7 N6 C3 N7 127.3(4) . . . . ?
O7 N6 C3 N4 3.6(5) . . . . ?
O7 N6 C3 N5 -117.8(4) . . . . ?
C2 N3 C1 N2 -0.3(4) . . . . ?
C2 N3 C1 N1 -178.2(3) . . . . ?
C2 N4 C3 N7 -56.5(5) . . . . ?
C2 N4 C3 N6 67.5(5) . . . . ?
C2 N4 C3 N5 -174.3(3) . . . . ?
C2 N8 N9 O4 179.4(4) . . . . ?
C2 N8 N9 O3 -2.9(6) . . . . ?
O10 N5 C3 N7 -11.3(5) . . . . ?
O10 N5 C3 N4 108.4(5) . . . . ?
O10 N5 C3 N6 -128.9(4) . . . . ?
C1 N3 C2 N4 -0.9(4) . . . . ?
C1 N3 C2 N8 178.3(5) . . . . ?
C1 N2 N4 C2 -1.9(4) . . . . ?
C1 N2 N4 C3 -175.0(3) . . . . ?
C3 N4 C2 N3 174.6(3) . . . . ?
C3 N4 C2 N8 -4.8(5) . . . . ?
_iucr_refine_instructions_details
;
mo_2016291_0m.res created by SHELXL-2014/7
TITL mo_2016291_0m_a.res in P2(1)
REM Old TITL mo_2016291_0m in P21 #4
REM SHELXT solution in P2(1)
REM R1 0.161, Rweak 0.036, Alpha 0.006, Orientation as input
REM Flack x = 0.355 ( 0.986 ) from Parsons' quotients
REM Formula found by SHELXT: C19 N O5
CELL 0.71073 7.8388 7.873 10.9873 90 90.413 90
ZERR 2 0.0015 0.0015 0.002 0 0.011 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 6 12 20 24
DFIX 1.42 O11A N10
DELU
ISOR 0.005 0.01 O1W O1WA
L.S. 10
PLAN 50
TEMP 23
FREE O11A H10c
FREE H10a H10c
damp
BOND $H
LIST 6
MORE -1
CONF
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM
REM
REM
WGHT 0.052400
BASF 0.29748
FVAR 1.32023 0.66710
N3 3 1.393097 1.180688 1.169142 11.00000 0.03680 0.04337 =
0.03554 0.00095 -0.00102 0.00323
N2 3 1.640661 1.079032 1.256520 11.00000 0.03763 0.04337 =
0.03786 0.00636 0.00155 0.00450
N7 3 1.775382 1.493782 1.315693 11.00000 0.04567 0.05422 =
0.04573 0.00543 -0.00319 -0.00311
O1 4 1.605794 0.788923 1.128729 11.00000 0.07525 0.04978 =
0.07342 -0.00897 -0.00816 0.02500
O2 4 1.380343 0.890693 1.036274 11.00000 0.06610 0.05673 =
0.06641 -0.01501 -0.01833 0.00514
N4 3 1.601691 1.238113 1.300849 11.00000 0.04222 0.04239 =
0.03909 -0.00314 -0.00748 0.00731
O4 4 1.244229 1.679244 1.251318 11.00000 0.07861 0.05514 =
0.08869 -0.00520 -0.00603 0.02845
N6 3 1.627328 1.372473 1.503716 11.00000 0.06434 0.05228 =
0.03883 0.00552 -0.00088 -0.00014
O5 4 1.794028 1.477160 1.207460 11.00000 0.07962 0.07329 =
0.04407 0.00896 0.01442 0.00787
N8 3 1.408412 1.457867 1.279681 11.00000 0.04317 0.04443 =
0.05176 -0.00541 -0.00975 0.01231
N1 3 1.498440 0.899601 1.110925 11.00000 0.05234 0.04257 =
0.04623 -0.00214 0.00040 0.00439
N9 3 1.282977 1.532485 1.216103 11.00000 0.04520 0.04528 =
0.06592 0.00431 -0.00853 0.00808
O3 4 1.212595 1.468442 1.127372 11.00000 0.08930 0.06002 =
0.11315 -0.00930 -0.06566 0.02004
O8 4 1.717051 1.452031 1.573936 11.00000 0.12263 0.07587 =
0.04483 -0.01076 -0.00391 -0.02131
O9 4 1.844710 1.103519 1.478824 11.00000 0.08647 0.07364 =
0.07189 0.02553 -0.02263 0.01259
N10 3 1.088071 2.139264 1.021232 11.00000 0.04048 0.05703 =
0.05924 -0.00294 -0.00196 0.00132
AFIX 7
H10A 2 1.168701 2.171649 1.070060 11.00000 -1.50000
H10B 2 1.136989 2.146030 0.941651 11.00000 -1.50000
AFIX 0
O6 4 1.799423 1.620800 1.376145 11.00000 0.10006 0.05900 =
0.07228 -0.00227 -0.00645 -0.01882
N5 3 1.871670 1.223112 1.411923 11.00000 0.04701 0.06388 =
0.05157 0.00463 -0.01228 0.00761
O7 4 1.487581 1.318892 1.520585 11.00000 0.06574 0.11722 =
0.05518 0.00243 0.01800 -0.00368
C2 1 1.452110 1.299903 1.245026 11.00000 0.03578 0.04129 =
0.03758 0.00271 -0.00315 0.00585
O10 4 2.005423 1.268200 1.367444 11.00000 0.05033 0.10318 =
0.11935 0.03004 -0.00591 0.01323
C1 1 1.511200 1.055808 1.182019 11.00000 0.03918 0.03660 =
0.03496 0.00435 0.00248 0.00429
C3 1 1.711244 1.328938 1.379774 11.00000 0.04247 0.04542 =
0.03847 0.00219 -0.00629 0.00020
PART 1
AFIX 6
O1W 4 0.973457 1.879285 1.178685 21.00000 0.05304 0.06795 =
0.08953 0.01650 -0.00984 0.00599
H1WA 2 1.059760 1.827811 1.207996 21.00000 -1.50000
H1WB 2 0.904566 1.902902 1.235631 21.00000 -1.50000
AFIX 0
O11 4 0.938250 2.236610 1.014352 10.50000 0.06977 0.05677 =
0.11204 -0.02012 -0.05140 0.01669
AFIX 147
H11 2 0.870554 2.191222 0.967318 10.50000 -1.50000
AFIX 0
PART 0
PART 2
O11A 4 0.949466 2.179318 1.082438 10.50000 0.06470 0.11145 =
0.11868 -0.04808 0.02847 0.02046
AFIX 83
H11A 2 0.933545 2.282106 1.078349 10.50000 -1.50000
AFIX 0
PART 0
H10C 2 1.037176 2.060446 1.077204 11.00000 0.12544
PART 2
AFIX 6
O1WA 4 0.987937 1.929218 1.248389 -21.00000 0.07517 0.10179 =
0.12111 -0.01472 0.00546 0.02508
H1WC 2 0.949066 1.994561 1.303178 -21.00000 -1.50000
H1WD 2 1.076004 1.878226 1.275339 -21.00000 -1.50000
AFIX 0
HKLF 4
REM mo_2016291_0m_a.res in P2(1)
REM R1 = 0.0426 for 2034 Fo > 4sig(Fo) and 0.0669 for all 2832 data
REM 258 parameters refined using 71 restraints
END
WGHT 0.0524 0.0000
REM Highest difference peak 0.219, deepest hole -0.227, 1-sigma level 0.046
Q1 1 1.3015 1.1879 1.1570 11.00000 0.05 0.22
Q2 1 1.8886 1.5370 1.3617 11.00000 0.05 0.19
Q3 1 1.4950 1.4784 1.2819 11.00000 0.05 0.19
Q4 1 1.3219 1.2594 1.0765 11.00000 0.05 0.18
Q5 1 1.0012 2.2922 0.9473 11.00000 0.05 0.17
Q6 1 1.2982 1.6774 1.2561 11.00000 0.05 0.16
Q7 1 1.5064 1.2208 1.4867 11.00000 0.05 0.16
Q8 1 1.4152 1.4785 1.2538 11.00000 0.05 0.16
Q9 1 1.8772 1.3774 1.3138 11.00000 0.05 0.16
Q10 1 1.3091 1.0751 1.1184 11.00000 0.05 0.15
Q11 1 1.8000 1.3658 1.5534 11.00000 0.05 0.15
Q12 1 1.8164 1.5905 1.5851 11.00000 0.05 0.15
Q13 1 1.9869 1.1542 1.3210 11.00000 0.05 0.14
Q14 1 1.6286 1.3104 1.3399 11.00000 0.05 0.14
Q15 1 1.7122 0.8836 1.1504 11.00000 0.05 0.14
Q16 1 1.6155 1.5059 1.5263 11.00000 0.05 0.14
Q17 1 1.0951 1.9982 1.0095 11.00000 0.05 0.14
Q18 1 1.1832 1.5969 1.2549 11.00000 0.05 0.13
Q19 1 1.3167 0.7630 0.8978 11.00000 0.05 0.13
Q20 1 1.3514 0.9813 1.0744 11.00000 0.05 0.13
Q21 1 2.1622 1.3180 1.2978 11.00000 0.05 0.13
Q22 1 1.6624 1.5999 1.2421 11.00000 0.05 0.13
Q23 1 1.6069 1.0659 1.2058 11.00000 0.05 0.13
Q24 1 1.1743 2.2636 1.0275 11.00000 0.05 0.13
Q25 1 2.1193 1.1604 1.3998 11.00000 0.05 0.13
Q26 1 1.4962 1.5509 1.3443 11.00000 0.05 0.13
Q27 1 1.4162 1.0826 1.1903 11.00000 0.05 0.13
Q28 1 1.7821 1.7638 1.4909 11.00000 0.05 0.13
Q29 1 1.5806 1.5200 1.2773 11.00000 0.05 0.12
Q30 1 1.6005 0.9031 1.1136 11.00000 0.05 0.12
Q31 1 1.4421 0.6795 1.1323 11.00000 0.05 0.12
Q32 1 1.4366 0.9253 1.3021 11.00000 0.05 0.12
Q33 1 1.4155 1.3839 1.2778 11.00000 0.05 0.12
Q34 1 1.4976 0.6495 1.0732 11.00000 0.05 0.12
Q35 1 2.1446 1.1796 1.2542 11.00000 0.05 0.12
Q36 1 1.6093 0.9214 1.2389 11.00000 0.05 0.12
Q37 1 0.8814 2.1184 0.9447 11.00000 0.05 0.12
Q38 1 1.7277 1.0731 1.2639 11.00000 0.05 0.12
Q39 1 1.5831 0.7783 1.1761 11.00000 0.05 0.12
Q40 1 1.3146 2.2746 1.0060 11.00000 0.05 0.12
Q41 1 1.2128 1.4658 1.0877 11.00000 0.05 0.12
Q42 1 1.3519 1.6436 1.2839 11.00000 0.05 0.12
Q43 1 1.1322 1.6453 1.2121 11.00000 0.05 0.12
Q44 1 1.5192 1.5703 1.5002 11.00000 0.05 0.11
Q45 1 1.2696 1.0137 1.0453 11.00000 0.05 0.11
Q46 1 1.4238 1.5400 1.3027 11.00000 0.05 0.11
Q47 1 1.4085 0.6618 1.0864 11.00000 0.05 0.11
Q48 1 2.0550 1.4344 1.2546 11.00000 0.05 0.11
Q49 1 1.3020 1.2611 1.4605 11.00000 0.05 0.11
Q50 1 1.6789 1.5892 1.1329 11.00000 0.05 0.11
REM The information below was added by Olex2.
REM
REM R1 = 0.0426 for 2034 Fo > 4sig(Fo) and 0.0669 for all 4232 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.22, deepest hole -0.23
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0669
REM R1_gt = 0.0426
REM wR_ref = 0.1210
REM GOOF = 1.006
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 4232
REM Reflections_gt = 2034
REM Parameters = n/a
REM Hole = -0.23
REM Peak = 0.22
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(2)
2 0(2)
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_mo_2016492_0m
_database_code_depnum_ccdc_archive 'CCDC 1506807'
_audit_update_record
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date 2017-07-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C3 H2 K N9 O11'
_chemical_formula_sum 'C3 H2 K N9 O11'
_chemical_formula_weight 379.24
_chemical_absolute_configuration ad
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 7.45940(10)
_cell_length_b 7.8789(2)
_cell_length_c 10.4774(2)
_cell_angle_alpha 90
_cell_angle_beta 90.7450(10)
_cell_angle_gamma 90
_cell_volume 615.72(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 3667
_cell_measurement_temperature 170
_cell_measurement_theta_max 25.521
_cell_measurement_theta_min 2.731
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.526
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.6325
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0588 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.8483. The \l/2 correction factor is 0.0015.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 2.046
_exptl_crystal_density_meas .
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 380
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.12
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0281
_diffrn_reflns_av_unetI/netI 0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 9574
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.532
_diffrn_reflns_theta_min 1.944
_diffrn_ambient_temperature 170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.769
_reflns_Friedel_fraction_full 0.937
_reflns_Friedel_fraction_max 0.885
_reflns_number_gt 2482
_reflns_number_total 2684
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection ?
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.204
_refine_diff_density_min -0.204
_refine_diff_density_rms 0.041
_refine_ls_abs_structure_details
;
Flack x determined using 1005 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.03(2)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.033
_refine_ls_hydrogen_treatment refxyz
_refine_ls_matrix_type full
_refine_ls_number_parameters 223
_refine_ls_number_reflns 2684
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0298
_refine_ls_R_factor_gt 0.0257
_refine_ls_restrained_S_all 1.033
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+0.0218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0543
_refine_ls_wR_factor_ref 0.0562
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.5 times of:
All O(H,H) groups
2. Restrained distances
H1WA-O1W = O1W-H1WB
0.85 with sigma of 0.02
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.43020(7) 0.55177(7) 0.01961(6) 0.02853(15) Uani 1 1 d . . . . .
O1 O 0.2885(2) 0.2479(3) 0.11153(19) 0.0296(4) Uani 1 1 d . . . . .
O1W O 0.5206(2) 0.8145(3) 0.1703(2) 0.0287(4) Uani 1 1 d D . . . .
H1WA H 0.447(4) 0.863(4) 0.214(3) 0.043 Uiso 1 1 d DR . . . .
H1WB H 0.609(4) 0.809(5) 0.217(3) 0.043 Uiso 1 1 d DR . . . .
O2 O 0.2715(2) 0.0534(3) 0.25757(18) 0.0305(4) Uani 1 1 d . . . A 1
O3 O 0.1467(2) 0.8419(2) 0.03383(19) 0.0298(4) Uani 1 1 d . . . . .
O4 O -0.0882(2) 0.9457(2) 0.12688(19) 0.0287(4) Uani 1 1 d . . . . .
O5 O -0.3566(2) 0.6305(3) 0.4709(2) 0.0342(5) Uani 1 1 d . . . . .
O6 O -0.5295(2) 0.4628(3) 0.3584(2) 0.0402(6) Uani 1 1 d . . . . .
O7 O 0.0119(3) 0.4122(3) 0.5251(2) 0.0361(5) Uani 1 1 d . . . . .
O8 O -0.2331(3) 0.2799(3) 0.57502(19) 0.0350(5) Uani 1 1 d . . . B 2
O9 O -0.3236(2) 0.2628(3) 0.19165(19) 0.0336(5) Uani 1 1 d . . . . .
O10 O -0.2997(2) 0.1086(2) 0.3628(2) 0.0318(5) Uani 1 1 d . . . . .
N1 N 0.2230(2) 0.1909(3) 0.2116(2) 0.0220(5) Uani 1 1 d . . . . .
N2 N 0.0926(3) 0.2692(3) 0.2757(2) 0.0228(5) Uani 1 1 d . . . . .
N3 N 0.1184(2) 0.5467(3) 0.16390(19) 0.0198(4) Uani 1 1 d . . . . .
N4 N 0.0204(3) 0.8322(3) 0.1069(2) 0.0227(5) Uani 1 1 d . . . . .
N5 N -0.1399(3) 0.6528(3) 0.2490(2) 0.0219(5) Uani 1 1 d . . . . .
N6 N -0.1047(3) 0.4921(3) 0.2934(2) 0.0207(5) Uani 1 1 d . . . . .
N7 N -0.1363(3) 0.3587(3) 0.5047(2) 0.0246(5) Uani 1 1 d . . . . .
N8 N -0.3877(3) 0.5095(3) 0.4035(2) 0.0249(5) Uani 1 1 d . . . . .
N9 N -0.2870(2) 0.2383(3) 0.3041(2) 0.0242(5) Uani 1 1 d . . . . .
C1 C 0.0504(3) 0.4278(3) 0.2387(2) 0.0198(5) Uani 1 1 d . . . . .
C2 C -0.0014(3) 0.6730(3) 0.1756(2) 0.0195(5) Uani 1 1 d . . . . .
C3 C -0.2208(3) 0.4022(3) 0.3727(3) 0.0211(5) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
K1 0.0308(3) 0.0219(3) 0.0331(4) -0.0012(3) 0.0095(2) -0.0039(2)
O1 0.0295(9) 0.0270(10) 0.0326(12) 0.0027(9) 0.0139(8) 0.0037(8)
O1W 0.0220(8) 0.0317(11) 0.0324(12) -0.0051(9) 0.0029(8) 0.0046(8)
O2 0.0348(9) 0.0232(9) 0.0337(12) 0.0038(10) 0.0040(8) 0.0125(9)
O3 0.0311(9) 0.0275(10) 0.0311(12) 0.0025(9) 0.0099(8) 0.0002(9)
O4 0.0304(9) 0.0236(11) 0.0323(12) -0.0009(9) 0.0028(8) 0.0077(8)
O5 0.0345(10) 0.0362(12) 0.0320(12) -0.0113(10) 0.0065(9) 0.0061(9)
O6 0.0196(8) 0.0416(13) 0.0596(16) -0.0113(12) 0.0003(9) 0.0033(9)
O7 0.0262(9) 0.0504(13) 0.0315(13) -0.0012(10) -0.0045(8) -0.0025(9)
O8 0.0473(11) 0.0330(12) 0.0248(11) 0.0046(9) 0.0053(9) -0.0097(9)
O9 0.0335(10) 0.0458(13) 0.0213(11) -0.0053(10) -0.0014(8) -0.0026(9)
O10 0.0347(10) 0.0248(11) 0.0360(12) -0.0019(9) 0.0035(8) -0.0027(8)
N1 0.0177(9) 0.0219(12) 0.0264(14) -0.0029(10) 0.0038(9) 0.0023(8)
N2 0.0212(9) 0.0222(12) 0.0252(13) 0.0020(10) 0.0065(9) 0.0047(8)
N3 0.0185(8) 0.0190(10) 0.0221(11) -0.0015(10) 0.0021(7) 0.0022(9)
N4 0.0231(10) 0.0219(11) 0.0230(12) -0.0012(10) 0.0001(9) 0.0013(9)
N5 0.0221(9) 0.0217(12) 0.0220(12) 0.0009(10) 0.0004(8) 0.0035(8)
N6 0.0181(9) 0.0211(11) 0.0231(12) 0.0041(9) 0.0055(8) 0.0039(8)
N7 0.0276(10) 0.0238(12) 0.0224(13) -0.0017(10) 0.0010(9) 0.0030(9)
N8 0.0232(10) 0.0273(13) 0.0244(13) 0.0012(10) 0.0064(9) 0.0040(9)
N9 0.0173(9) 0.0275(13) 0.0278(14) -0.0061(11) 0.0047(9) 0.0010(9)
C1 0.0160(10) 0.0228(13) 0.0206(14) -0.0026(11) 0.0030(10) 0.0022(10)
C2 0.0212(11) 0.0192(12) 0.0180(14) -0.0012(10) -0.0013(9) 0.0002(10)
C3 0.0178(10) 0.0248(13) 0.0209(14) 0.0001(11) 0.0029(10) 0.0024(10)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 K1 4.0968(3) 2_645 ?
K1 K1 4.0968(3) 2_655 ?
K1 O1 2.9588(18) 2_655 ?
K1 O1 2.793(2) . ?
K1 O1W 2.684(2) . ?
K1 O1W 2.758(2) 2_645 ?
K1 O3 3.1190(19) . ?
K1 O4 3.0760(19) 2_545 ?
K1 O9 2.872(2) 2 ?
K1 O9 3.423(2) 1_655 ?
K1 N3 2.7904(19) . ?
O1 K1 2.9588(18) 2_645 ?
O1 N1 1.247(3) . ?
O1W K1 2.758(2) 2_655 ?
O1W H1WA 0.82(2) . ?
O1W H1WB 0.82(2) . ?
O2 N1 1.238(3) . ?
O3 N4 1.224(3) . ?
O4 K1 3.0760(19) 2 ?
O4 N4 1.226(3) . ?
O5 N8 1.207(3) . ?
O6 N8 1.211(3) . ?
O7 N7 1.200(3) . ?
O8 N7 1.210(3) . ?
O9 K1 3.423(2) 1_455 ?
O9 K1 2.872(2) 2_545 ?
O9 N9 1.221(3) . ?
O10 N9 1.197(3) . ?
N1 N2 1.339(3) . ?
N2 C1 1.344(3) . ?
N3 C1 1.327(3) . ?
N3 C2 1.344(3) . ?
N4 C2 1.457(3) . ?
N5 N6 1.373(3) . ?
N5 C2 1.306(3) . ?
N6 C1 1.394(3) . ?
N6 C3 1.400(3) . ?
N7 C3 1.551(3) . ?
N8 C3 1.542(3) . ?
N9 C3 1.555(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
K1 K1 K1 148.14(3) 2_645 2_655 ?
O1 K1 K1 46.23(4) . 2_645 ?
O1 K1 K1 42.98(4) 2_655 2_655 ?
O1 K1 K1 105.84(4) 2_655 2_645 ?
O1 K1 K1 163.05(5) . 2_655 ?
O1 K1 O1 151.84(6) . 2_655 ?
O1 K1 O3 97.16(5) 2_655 . ?
O1 K1 O3 110.60(5) . . ?
O1 K1 O4 119.92(6) 2_655 2_545 ?
O1 K1 O4 67.92(5) . 2_545 ?
O1 K1 O9 131.27(6) . 2 ?
O1 K1 O9 102.31(5) 2_655 1_655 ?
O1 K1 O9 56.72(5) . 1_655 ?
O1W K1 K1 40.50(4) 2_645 2_645 ?
O1W K1 K1 41.86(5) . 2_655 ?
O1W K1 K1 122.88(5) 2_645 2_655 ?
O1W K1 K1 137.59(5) . 2_645 ?
O1W K1 O1 72.30(6) . 2_655 ?
O1W K1 O1 123.47(6) . . ?
O1W K1 O1 73.88(6) 2_645 . ?
O1W K1 O1 85.25(6) 2_645 2_655 ?
O1W K1 O1W 155.82(3) . 2_645 ?
O1W K1 O3 64.66(5) . . ?
O1W K1 O3 128.89(6) 2_645 . ?
O1W K1 O4 134.70(5) . 2_545 ?
O1W K1 O4 64.73(5) 2_645 2_545 ?
O1W K1 O9 81.59(6) 2_645 1_655 ?
O1W K1 O9 94.26(6) . 1_655 ?
O1W K1 O9 82.78(6) 2_645 2 ?
O1W K1 O9 94.11(6) . 2 ?
O1W K1 N3 84.10(6) . . ?
O1W K1 N3 120.05(6) 2_645 . ?
O3 K1 K1 152.00(4) . 2_645 ?
O3 K1 K1 58.22(3) . 2_655 ?
O3 K1 O9 145.26(5) . 1_655 ?
O4 K1 K1 84.20(4) 2_545 2_645 ?
O4 K1 K1 114.93(4) 2_545 2_655 ?
O4 K1 O3 70.40(5) 2_545 . ?
O4 K1 O9 121.18(5) 2_545 1_655 ?
O9 K1 K1 123.19(5) 2 2_645 ?
O9 K1 K1 43.78(4) 1_655 2_645 ?
O9 K1 K1 55.54(4) 2 2_655 ?
O9 K1 K1 123.85(4) 1_655 2_655 ?
O9 K1 O1 62.00(5) 2 2_655 ?
O9 K1 O3 55.35(6) 2 . ?
O9 K1 O4 63.47(5) 2 2_545 ?
O9 K1 O9 158.74(3) 2 1_655 ?
N3 K1 K1 106.43(5) . 2_655 ?
N3 K1 K1 104.79(5) . 2_645 ?
N3 K1 O1 58.61(6) . . ?
N3 K1 O1 149.33(7) . 2_655 ?
N3 K1 O3 54.15(6) . . ?
N3 K1 O4 64.83(5) . 2_545 ?
N3 K1 O9 101.62(6) . 2 ?
N3 K1 O9 98.65(6) . 1_655 ?
K1 O1 K1 90.79(5) . 2_645 ?
N1 O1 K1 138.86(16) . . ?
N1 O1 K1 119.39(15) . 2_645 ?
K1 O1W K1 97.65(7) . 2_655 ?
K1 O1W H1WA 101(3) 2_655 . ?
K1 O1W H1WA 122(2) . . ?
K1 O1W H1WB 120(3) . . ?
K1 O1W H1WB 111(3) 2_655 . ?
H1WA O1W H1WB 104(3) . . ?
N4 O3 K1 120.80(16) . . ?
N4 O4 K1 131.16(15) . 2 ?
K1 O9 K1 80.68(5) 2_545 1_455 ?
N9 O9 K1 136.44(16) . 1_455 ?
N9 O9 K1 135.10(17) . 2_545 ?
O1 N1 N2 123.4(2) . . ?
O2 N1 O1 121.8(2) . . ?
O2 N1 N2 114.8(2) . . ?
N1 N2 C1 116.9(2) . . ?
C1 N3 K1 131.14(15) . . ?
C1 N3 C2 102.07(19) . . ?
C2 N3 K1 126.79(17) . . ?
O3 N4 O4 125.2(2) . . ?
O3 N4 C2 117.0(2) . . ?
O4 N4 C2 117.7(2) . . ?
C2 N5 N6 99.3(2) . . ?
N5 N6 C1 110.6(2) . . ?
N5 N6 C3 123.4(2) . . ?
C1 N6 C3 125.7(2) . . ?
O7 N7 O8 128.9(2) . . ?
O7 N7 C3 116.4(2) . . ?
O8 N7 C3 114.7(2) . . ?
O5 N8 O6 128.9(2) . . ?
O5 N8 C3 114.0(2) . . ?
O6 N8 C3 117.1(2) . . ?
O9 N9 C3 112.4(2) . . ?
O10 N9 O9 127.7(2) . . ?
O10 N9 C3 119.9(2) . . ?
N2 C1 N6 114.3(2) . . ?
N3 C1 N2 137.5(2) . . ?
N3 C1 N6 108.2(2) . . ?
N3 C2 N4 120.9(2) . . ?
N5 C2 N3 119.7(2) . . ?
N5 C2 N4 119.3(2) . . ?
N6 C3 N7 113.17(19) . . ?
N6 C3 N8 110.7(2) . . ?
N6 C3 N9 109.9(2) . . ?
N7 C3 N9 110.6(2) . . ?
N8 C3 N7 104.7(2) . . ?
N8 C3 N9 107.44(18) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 O1 N1 O2 -132.5(2) . . . . ?
K1 O1 N1 O2 -0.5(3) 2_645 . . . ?
K1 O1 N1 N2 -178.53(16) 2_645 . . . ?
K1 O1 N1 N2 49.5(3) . . . . ?
K1 O3 N4 O4 173.35(17) . . . . ?
K1 O3 N4 C2 -6.4(3) . . . . ?
K1 O4 N4 O3 83.6(3) 2 . . . ?
K1 O4 N4 C2 -96.6(2) 2 . . . ?
K1 O9 N9 O10 129.9(2) 1_455 . . . ?
K1 O9 N9 O10 -6.4(4) 2_545 . . . ?
K1 O9 N9 C3 -48.8(3) 1_455 . . . ?
K1 O9 N9 C3 174.96(14) 2_545 . . . ?
K1 N3 C1 N2 -1.0(4) . . . . ?
K1 N3 C1 N6 177.35(14) . . . . ?
K1 N3 C2 N4 1.7(3) . . . . ?
K1 N3 C2 N5 -178.67(16) . . . . ?
O1 N1 N2 C1 -9.6(3) . . . . ?
O2 N1 N2 C1 172.3(2) . . . . ?
O3 N4 C2 N3 3.6(3) . . . . ?
O3 N4 C2 N5 -176.1(2) . . . . ?
O4 N4 C2 N3 -176.2(2) . . . . ?
O4 N4 C2 N5 4.2(3) . . . . ?
O5 N8 C3 N6 -68.6(3) . . . . ?
O5 N8 C3 N7 53.7(3) . . . . ?
O5 N8 C3 N9 171.3(2) . . . . ?
O6 N8 C3 N6 111.5(3) . . . . ?
O6 N8 C3 N7 -126.2(2) . . . . ?
O6 N8 C3 N9 -8.6(3) . . . . ?
O7 N7 C3 N6 3.1(3) . . . . ?
O7 N7 C3 N8 -117.6(2) . . . . ?
O7 N7 C3 N9 127.0(2) . . . . ?
O8 N7 C3 N6 -179.5(2) . . . . ?
O8 N7 C3 N8 59.8(3) . . . . ?
O8 N7 C3 N9 -55.6(3) . . . . ?
O9 N9 C3 N6 -41.7(3) . . . . ?
O9 N9 C3 N7 -167.35(18) . . . . ?
O9 N9 C3 N8 78.9(2) . . . . ?
O10 N9 C3 N6 139.6(2) . . . . ?
O10 N9 C3 N7 13.9(3) . . . . ?
O10 N9 C3 N8 -99.9(2) . . . . ?
N1 N2 C1 N3 -12.0(4) . . . . ?
N1 N2 C1 N6 169.7(2) . . . . ?
N5 N6 C1 N2 -178.95(19) . . . . ?
N5 N6 C1 N3 2.3(3) . . . . ?
N5 N6 C3 N7 -118.2(2) . . . . ?
N5 N6 C3 N8 -1.0(3) . . . . ?
N5 N6 C3 N9 117.6(2) . . . . ?
N6 N5 C2 N3 1.1(3) . . . . ?
N6 N5 C2 N4 -179.2(2) . . . . ?
C1 N3 C2 N4 -179.4(2) . . . . ?
C1 N3 C2 N5 0.2(3) . . . . ?
C1 N6 C3 N7 68.6(3) . . . . ?
C1 N6 C3 N8 -174.2(2) . . . . ?
C1 N6 C3 N9 -55.6(3) . . . . ?
C2 N3 C1 N2 -179.8(3) . . . . ?
C2 N3 C1 N6 -1.5(3) . . . . ?
C2 N5 N6 C1 -2.0(2) . . . . ?
C2 N5 N6 C3 -176.1(2) . . . . ?
C3 N6 C1 N2 -5.0(3) . . . . ?
C3 N6 C1 N3 176.2(2) . . . . ?
_shelx_res_file
;
mo_2016492_0m.res created by SHELXL-2014/7
TITL mo_2016492_0m_a.res in P2(1)
REM Old TITL mo_2016492_0m in P2(1)
REM SHELXT solution in P2(1)
REM R1 0.092, Rweak 0.024, Alpha 0.004, Orientation as input
REM Flack x = 0.050 ( 0.020 ) from Parsons' quotients
REM Formula found by SHELXT: C13 N5 O5 K
CELL 0.71073 7.4594 7.8789 10.4774 90 90.745 90
ZERR 2 0.0001 0.0002 0.0002 0 0.001 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H K N O
UNIT 6 4 2 18 22
DFIX 0.85 H1Wa O1W O1W H1Wb
L.S. 20 0 0
PLAN 20
TEMP -103.15
BOND $H
list 4
CONF
fmap 2
acta
OMIT -2 0 7
REM
REM
REM
WGHT 0.027200 0.021800
FVAR 1.14433
K1 3 0.430203 0.551769 0.019615 11.00000 0.03076 0.02192 =
0.03315 -0.00116 0.00946 -0.00389
O1 5 0.288500 0.247934 0.111525 11.00000 0.02951 0.02705 =
0.03262 0.00266 0.01389 0.00368
O1W 5 0.520627 0.814524 0.170309 11.00000 0.02204 0.03174 =
0.03239 -0.00513 0.00291 0.00461
H1WA 2 0.446872 0.862546 0.214292 11.00000 -1.50000
H1WB 2 0.609274 0.808599 0.216762 11.00000 -1.50000
PART 1
O2 5 0.271456 0.053418 0.257574 11.00000 0.03479 0.02320 =
0.03368 0.00383 0.00402 0.01246
PART 0
O3 5 0.146726 0.841930 0.033826 11.00000 0.03112 0.02754 =
0.03105 0.00255 0.00989 0.00019
O4 5 -0.088173 0.945699 0.126881 11.00000 0.03045 0.02355 =
0.03231 -0.00090 0.00280 0.00772
O5 5 -0.356646 0.630540 0.470950 11.00000 0.03451 0.03620 =
0.03202 -0.01132 0.00650 0.00615
O6 5 -0.529505 0.462824 0.358363 11.00000 0.01958 0.04158 =
0.05956 -0.01134 0.00032 0.00328
O7 5 0.011861 0.412245 0.525142 11.00000 0.02621 0.05042 =
0.03147 -0.00120 -0.00447 -0.00249
PART 2
O8 5 -0.233114 0.279870 0.575019 11.00000 0.04732 0.03299 =
0.02477 0.00457 0.00528 -0.00970
PART 0
O9 5 -0.323638 0.262800 0.191647 11.00000 0.03353 0.04583 =
0.02132 -0.00534 -0.00138 -0.00264
O10 5 -0.299667 0.108609 0.362800 11.00000 0.03465 0.02479 =
0.03599 -0.00190 0.00353 -0.00270
N1 4 0.222973 0.190927 0.211634 11.00000 0.01769 0.02187 =
0.02643 -0.00292 0.00383 0.00230
N2 4 0.092641 0.269249 0.275711 11.00000 0.02118 0.02219 =
0.02517 0.00197 0.00650 0.00471
N3 4 0.118447 0.546719 0.163897 11.00000 0.01854 0.01895 =
0.02209 -0.00152 0.00213 0.00219
N4 4 0.020373 0.832229 0.106892 11.00000 0.02310 0.02187 =
0.02305 -0.00121 0.00008 0.00130
N5 4 -0.139935 0.652837 0.249043 11.00000 0.02209 0.02170 =
0.02198 0.00088 0.00037 0.00346
N6 4 -0.104702 0.492126 0.293424 11.00000 0.01814 0.02106 =
0.02305 0.00407 0.00551 0.00395
N7 4 -0.136326 0.358703 0.504724 11.00000 0.02759 0.02385 =
0.02239 -0.00171 0.00101 0.00295
N8 4 -0.387659 0.509494 0.403524 11.00000 0.02317 0.02728 =
0.02438 0.00116 0.00639 0.00403
N9 4 -0.287004 0.238341 0.304098 11.00000 0.01725 0.02751 =
0.02782 -0.00611 0.00475 0.00102
C1 1 0.050415 0.427757 0.238659 11.00000 0.01600 0.02283 =
0.02065 -0.00264 0.00298 0.00222
C2 1 -0.001400 0.672980 0.175607 11.00000 0.02122 0.01919 =
0.01803 -0.00116 -0.00129 0.00018
C3 1 -0.220825 0.402204 0.372695 11.00000 0.01777 0.02482 =
0.02086 0.00015 0.00288 0.00238
HKLF 4
REM mo_2016492_0m_a.res in P2(1)
REM R1 = 0.0257 for 2482 Fo > 4sig(Fo) and 0.0298 for all 2684 data
REM 223 parameters refined using 3 restraints
END
WGHT 0.0272 0.0218
REM Highest difference peak 0.204, deepest hole -0.204, 1-sigma level 0.041
Q1 1 -0.1565 0.4437 0.3182 11.00000 0.05 0.20
Q2 1 -0.2480 0.3271 0.3344 11.00000 0.05 0.18
Q3 1 0.0054 0.7415 0.1392 11.00000 0.05 0.16
Q4 1 0.5015 0.5494 0.0948 11.00000 0.05 0.16
Q5 1 -0.0229 0.4505 0.2598 11.00000 0.05 0.16
Q6 1 -0.1798 0.3622 0.4328 11.00000 0.05 0.16
Q7 1 -0.0606 0.6793 0.2172 11.00000 0.05 0.15
Q8 1 -0.5031 0.4298 0.2464 11.00000 0.05 0.14
Q9 1 -0.6028 0.3809 0.2834 11.00000 0.05 0.13
Q10 1 0.2174 0.2610 -0.0105 11.00000 0.05 0.13
Q11 1 0.1890 0.2548 0.0387 11.00000 0.05 0.13
Q12 1 0.2867 0.4964 -0.0221 11.00000 0.05 0.13
Q13 1 -0.0898 0.9224 0.1983 11.00000 0.05 0.13
Q14 1 0.2054 0.3677 0.6375 11.00000 0.05 0.13
Q15 1 0.1839 0.9287 0.0244 11.00000 0.05 0.12
Q16 1 0.3376 0.0442 0.2129 11.00000 0.05 0.12
Q17 1 0.3712 0.6084 -0.0487 11.00000 0.05 0.12
Q18 1 0.4683 0.1447 0.2589 11.00000 0.05 0.12
Q19 1 0.3642 0.0470 0.3198 11.00000 0.05 0.12
Q20 1 0.2901 0.2728 0.0818 11.00000 0.05 0.12
;
_shelx_res_checksum 46296
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_a
_database_code_depnum_ccdc_archive 'CCDC 1506808'
_audit_update_record
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date 2017-07-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C3 N9 O10, H2 O, H4 N'
_chemical_formula_sum 'C3 H6 N10 O11'
_chemical_formula_weight 358.18
_chemical_absolute_configuration .
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 7.5643(7)
_cell_length_b 8.0022(7)
_cell_length_c 10.6515(10)
_cell_angle_alpha 90
_cell_angle_beta 91.239(2)
_cell_angle_gamma 90
_cell_volume 644.60(10)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 1424
_cell_measurement_temperature 296.15
_cell_measurement_theta_max 25.107
_cell_measurement_theta_min 3.184
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.184
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear yellowish yellow'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier yellowish
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.845
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 364
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.2
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0141
_diffrn_reflns_av_unetI/netI 0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 3901
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.553
_diffrn_reflns_theta_min 2.693
_diffrn_ambient_temperature 296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.762
_reflns_Friedel_fraction_full 0.945
_reflns_Friedel_fraction_max 0.862
_reflns_number_gt 2298
_reflns_number_total 2752
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection ?
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.141
_refine_diff_density_min -0.175
_refine_diff_density_rms 0.039
_refine_ls_abs_structure_details
;
Flack x determined using 856 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.6(8)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.023
_refine_ls_hydrogen_treatment refxyz
_refine_ls_matrix_type full
_refine_ls_number_parameters 235
_refine_ls_number_reflns 2752
_refine_ls_number_restraints 7
_refine_ls_R_factor_all 0.0482
_refine_ls_R_factor_gt 0.0355
_refine_ls_restrained_S_all 1.023
_refine_ls_shift/su_max 0.008
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+0.0561P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0739
_refine_ls_wR_factor_ref 0.0796
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.5 times of:
All N(H,H,H,H) groups, All O(H,H) groups
2. Restrained distances
N10-H10A = N10-H10B = N10-H10C = N10-H10D
0.88 with sigma of 0.02
O1W-H1WB = O1W-H1WA
0.85 with sigma of 0.02
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2168(3) -0.5038(3) -0.1210(3) 0.0510(7) Uani 1 1 d . . . . .
O1W O -0.0253(3) -0.0963(4) -0.1818(3) 0.0561(7) Uani 1 1 d D . . . .
H1WA H 0.056(5) -0.147(6) -0.215(5) 0.084 Uiso 1 1 d DR . . . .
H1WB H -0.122(4) -0.114(7) -0.219(4) 0.084 Uiso 1 1 d DR . . . .
O2 O 0.2391(3) -0.3113(3) -0.2612(3) 0.0543(7) Uani 1 1 d . . . A 1
O3 O 0.3563(3) -1.0886(3) -0.0382(2) 0.0512(6) Uani 1 1 d . . . . .
O4 O 0.5889(3) -1.1902(3) -0.1271(3) 0.0502(6) Uani 1 1 d . . . . .
O5 O 0.8181(3) -0.5182(4) -0.1951(2) 0.0528(7) Uani 1 1 d . . . . .
O6 O 0.8008(3) -0.3722(3) -0.3658(3) 0.0553(7) Uani 1 1 d . . . . .
O7 O 0.7277(4) -0.5409(3) -0.5725(2) 0.0596(8) Uani 1 1 d . . . B 2
O8 O 0.4872(3) -0.6696(4) -0.5231(2) 0.0593(8) Uani 1 1 d . . . . .
O9 O 0.8506(3) -0.8844(3) -0.4695(3) 0.0556(7) Uani 1 1 d . . . . .
O10 O 1.0192(3) -0.7247(4) -0.3545(3) 0.0674(9) Uani 1 1 d . . . . .
N1 N 0.3860(3) -0.7977(3) -0.1664(2) 0.0303(6) Uani 1 1 d . . . . .
N2 N 0.6394(3) -0.9042(3) -0.2492(2) 0.0317(6) Uani 1 1 d . . . . .
N3 N 0.6049(3) -0.7458(3) -0.2941(3) 0.0323(6) Uani 1 1 d . . . . .
N4 N 0.4117(3) -0.5256(3) -0.2780(3) 0.0368(6) Uani 1 1 d . . . . .
N5 N 0.2840(3) -0.4482(3) -0.2168(3) 0.0359(6) Uani 1 1 d . . . . .
N6 N 0.4819(4) -1.0800(3) -0.1094(3) 0.0372(6) Uani 1 1 d . . . . .
N7 N 0.7856(3) -0.4976(4) -0.3063(3) 0.0367(6) Uani 1 1 d . . . . .
N8 N 0.6334(4) -0.6181(3) -0.5025(2) 0.0380(6) Uani 1 1 d . . . . .
N9 N 0.8814(3) -0.7672(4) -0.4019(3) 0.0392(7) Uani 1 1 d . . . . .
N10 N 0.0483(5) 0.1877(4) -0.0397(4) 0.0505(8) Uani 1 1 d D . . . .
H10A H 0.153(4) 0.227(6) -0.059(5) 0.076 Uiso 1 1 d DR . . . .
H10B H -0.001(6) 0.100(5) -0.073(4) 0.076 Uiso 1 1 d DR . . . .
H10C H -0.014(6) 0.263(5) -0.081(4) 0.076 Uiso 1 1 d DR . . . .
H10D H 0.071(6) 0.176(7) 0.037(3) 0.076 Uiso 1 1 d DR . . . .
C1 C 0.4525(4) -0.6816(4) -0.2407(3) 0.0295(6) Uani 1 1 d . . . . .
C2 C 0.5033(4) -0.9233(4) -0.1773(3) 0.0297(7) Uani 1 1 d . . . . .
C3 C 0.7183(4) -0.6594(4) -0.3726(3) 0.0312(7) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0496(14) 0.0423(13) 0.0623(16) 0.0019(13) 0.0299(13) 0.0084(12)
O1W 0.0369(15) 0.0608(17) 0.0705(19) -0.0180(15) 0.0025(13) 0.0052(14)
O2 0.0594(15) 0.0417(14) 0.0622(18) 0.0050(13) 0.0066(13) 0.0266(13)
O3 0.0520(14) 0.0492(14) 0.0531(15) 0.0101(13) 0.0176(12) 0.0024(13)
O4 0.0511(14) 0.0384(13) 0.0613(16) 0.0046(12) 0.0085(12) 0.0117(12)
O5 0.0571(16) 0.0667(17) 0.0343(14) -0.0099(12) -0.0059(12) -0.0017(13)
O6 0.0695(17) 0.0396(14) 0.0570(17) 0.0000(14) 0.0029(14) -0.0112(13)
O7 0.085(2) 0.0584(18) 0.0353(13) 0.0078(13) 0.0056(13) -0.0160(15)
O8 0.0433(14) 0.089(2) 0.0453(15) -0.0053(15) -0.0113(12) -0.0005(15)
O9 0.0567(16) 0.0575(16) 0.0530(16) -0.0173(14) 0.0111(14) 0.0147(14)
O10 0.0289(13) 0.080(2) 0.093(2) -0.0196(18) -0.0008(14) 0.0110(13)
N1 0.0253(12) 0.0321(13) 0.0335(14) -0.0025(11) 0.0023(10) 0.0013(11)
N2 0.0295(13) 0.0329(15) 0.0328(14) 0.0000(11) 0.0028(11) 0.0067(10)
N3 0.0283(13) 0.0336(13) 0.0351(14) 0.0038(11) 0.0061(11) 0.0048(11)
N4 0.0330(13) 0.0340(15) 0.0438(16) 0.0049(12) 0.0100(12) 0.0090(11)
N5 0.0285(13) 0.0361(15) 0.0432(16) -0.0021(13) 0.0048(12) 0.0047(11)
N6 0.0396(15) 0.0347(14) 0.0371(15) 0.0006(12) 0.0013(13) 0.0039(13)
N7 0.0260(13) 0.0467(17) 0.0376(16) -0.0081(14) 0.0028(11) 0.0013(12)
N8 0.0455(16) 0.0380(15) 0.0305(14) -0.0035(12) 0.0010(13) 0.0030(13)
N9 0.0329(15) 0.0458(18) 0.0392(16) 0.0000(14) 0.0099(12) 0.0068(12)
N10 0.0497(18) 0.0425(17) 0.060(2) 0.0034(17) 0.0094(17) -0.0057(15)
C1 0.0238(13) 0.0340(16) 0.0309(16) -0.0036(14) 0.0037(12) 0.0040(13)
C2 0.0295(15) 0.0311(16) 0.0285(15) -0.0007(13) -0.0012(12) -0.0003(12)
C3 0.0287(14) 0.0370(17) 0.0283(15) -0.0010(13) 0.0062(12) 0.0038(13)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N5 1.232(4) . ?
O1W H1WA 0.83(3) . ?
O1W H1WB 0.84(2) . ?
O2 N5 1.238(4) . ?
O3 N6 1.231(3) . ?
O4 N6 1.214(3) . ?
O5 N7 1.216(4) . ?
O6 N7 1.194(4) . ?
O7 N8 1.212(4) . ?
O8 N8 1.196(4) . ?
O9 N9 1.202(4) . ?
O10 N9 1.198(4) . ?
N1 C1 1.326(4) . ?
N1 C2 1.347(4) . ?
N2 N3 1.377(4) . ?
N2 C2 1.305(4) . ?
N3 C1 1.395(4) . ?
N3 C3 1.395(4) . ?
N4 N5 1.331(3) . ?
N4 C1 1.344(4) . ?
N6 C2 1.458(4) . ?
N7 C3 1.555(4) . ?
N8 C3 1.548(4) . ?
N9 C3 1.543(4) . ?
N10 H10A 0.88(2) . ?
N10 H10B 0.87(3) . ?
N10 H10C 0.88(2) . ?
N10 H10D 0.84(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1WA O1W H1WB 111(5) . . ?
C1 N1 C2 102.3(2) . . ?
C2 N2 N3 99.5(2) . . ?
N2 N3 C1 110.5(2) . . ?
N2 N3 C3 123.3(2) . . ?
C3 N3 C1 125.9(2) . . ?
N5 N4 C1 116.8(3) . . ?
O1 N5 O2 121.4(3) . . ?
O1 N5 N4 123.7(3) . . ?
O2 N5 N4 114.9(3) . . ?
O3 N6 C2 116.7(3) . . ?
O4 N6 O3 125.5(3) . . ?
O4 N6 C2 117.8(3) . . ?
O5 N7 C3 112.7(3) . . ?
O6 N7 O5 127.7(3) . . ?
O6 N7 C3 119.6(3) . . ?
O7 N8 C3 114.8(3) . . ?
O8 N8 O7 128.1(3) . . ?
O8 N8 C3 117.0(3) . . ?
O9 N9 C3 114.3(3) . . ?
O10 N9 O9 129.0(3) . . ?
O10 N9 C3 116.7(3) . . ?
H10A N10 H10B 125(5) . . ?
H10A N10 H10C 97(4) . . ?
H10A N10 H10D 96(4) . . ?
H10B N10 H10C 97(4) . . ?
H10B N10 H10D 113(5) . . ?
H10C N10 H10D 132(5) . . ?
N1 C1 N3 108.2(2) . . ?
N1 C1 N4 137.8(3) . . ?
N4 C1 N3 114.0(3) . . ?
N1 C2 N6 121.2(3) . . ?
N2 C2 N1 119.5(3) . . ?
N2 C2 N6 119.3(3) . . ?
N3 C3 N7 109.9(2) . . ?
N3 C3 N8 113.1(2) . . ?
N3 C3 N9 110.4(2) . . ?
N8 C3 N7 110.7(2) . . ?
N9 C3 N7 107.6(2) . . ?
N9 C3 N8 104.9(2) . . ?
_shelx_res_file
;
a.res created by SHELXL-2014/7
TITL a_a.res in P2(1)
REM Old TITL a in P21 #4
REM SHELXT solution in P2(1)
REM R1 0.126, Rweak 0.045, Alpha 0.003, Orientation as input
REM Flack x = -0.754 ( 0.581 ) from Parsons' quotients
REM Formula found by SHELXT: C16 N3 O5
CELL 0.71073 7.5643 8.0022 10.6515 90 91.239 90
ZERR 2 0.0007 0.0007 0.001 0 0.002 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 6 12 20 22
DFIX 0.88 N10 H10a N10 H10b N10 H10c N10 H10d
DFIX 0.85 O1W H1Wb O1W H1Wa
L.S. 5
PLAN 20
TEMP 23
BOND $H
fmap 2
acta
OMIT 0 0 1
REM
REM
REM
WGHT 0.037200 0.056100
FVAR 1.22450
O1 4 0.216839 -0.503791 -0.120995 11.00000 0.04964 0.04228 =
0.06229 0.00189 0.02992 0.00837
O1W 4 -0.025322 -0.096265 -0.181767 11.00000 0.03693 0.06085 =
0.07053 -0.01800 0.00247 0.00520
H1WA 2 0.056114 -0.146956 -0.215360 11.00000 -1.50000
H1WB 2 -0.121917 -0.114498 -0.218889 11.00000 -1.50000
PART 1
O2 4 0.239085 -0.311271 -0.261248 11.00000 0.05936 0.04165 =
0.06218 0.00498 0.00661 0.02656
PART 0
O3 4 0.356278 -1.088615 -0.038173 11.00000 0.05198 0.04915 =
0.05311 0.01009 0.01762 0.00237
O4 4 0.588927 -1.190211 -0.127090 11.00000 0.05110 0.03838 =
0.06133 0.00463 0.00849 0.01174
O5 4 0.818080 -0.518250 -0.195059 11.00000 0.05715 0.06674 =
0.03425 -0.00989 -0.00588 -0.00172
O6 4 0.800849 -0.372210 -0.365825 11.00000 0.06945 0.03957 =
0.05696 0.00005 0.00286 -0.01120
PART 2
O7 4 0.727717 -0.540943 -0.572484 11.00000 0.08541 0.05841 =
0.03532 0.00777 0.00557 -0.01601
PART 0
O8 4 0.487161 -0.669586 -0.523100 11.00000 0.04327 0.08891 =
0.04526 -0.00528 -0.01129 -0.00048
O9 4 0.850591 -0.884359 -0.469528 11.00000 0.05665 0.05755 =
0.05298 -0.01726 0.01115 0.01474
O10 4 1.019241 -0.724725 -0.354503 11.00000 0.02891 0.07985 =
0.09343 -0.01965 -0.00079 0.01102
N1 3 0.386047 -0.797747 -0.166392 11.00000 0.02533 0.03211 =
0.03347 -0.00248 0.00234 0.00132
N2 3 0.639437 -0.904155 -0.249208 11.00000 0.02950 0.03294 =
0.03279 -0.00001 0.00275 0.00669
N3 3 0.604899 -0.745821 -0.294095 11.00000 0.02835 0.03359 =
0.03511 0.00382 0.00610 0.00480
N4 3 0.411725 -0.525611 -0.278040 11.00000 0.03299 0.03405 =
0.04380 0.00493 0.01004 0.00899
N5 3 0.283973 -0.448216 -0.216782 11.00000 0.02855 0.03609 =
0.04320 -0.00211 0.00478 0.00469
N6 3 0.481935 -1.080031 -0.109402 11.00000 0.03963 0.03474 =
0.03714 0.00060 0.00129 0.00395
N7 3 0.785620 -0.497609 -0.306328 11.00000 0.02599 0.04671 =
0.03759 -0.00813 0.00285 0.00130
N8 3 0.633353 -0.618079 -0.502510 11.00000 0.04547 0.03796 =
0.03052 -0.00354 0.00104 0.00303
N9 3 0.881411 -0.767219 -0.401904 11.00000 0.03295 0.04581 =
0.03917 0.00002 0.00991 0.00678
N10 3 0.048268 0.187678 -0.039732 11.00000 0.04966 0.04249 =
0.05977 0.00341 0.00937 -0.00572
H10A 2 0.152924 0.226532 -0.059272 11.00000 -1.50000
H10B 2 -0.001060 0.099598 -0.072757 11.00000 -1.50000
H10C 2 -0.014036 0.262700 -0.081487 11.00000 -1.50000
H10D 2 0.070978 0.176300 0.037125 11.00000 -1.50000
C1 1 0.452451 -0.681601 -0.240652 11.00000 0.02378 0.03405 =
0.03090 -0.00356 0.00365 0.00400
C2 1 0.503344 -0.923318 -0.177309 11.00000 0.02954 0.03109 =
0.02849 -0.00075 -0.00121 -0.00026
C3 1 0.718310 -0.659439 -0.372634 11.00000 0.02870 0.03695 =
0.02831 -0.00104 0.00617 0.00385
HKLF 4
REM a_a.res in P2(1)
REM R1 = 0.0355 for 2298 Fo > 4sig(Fo) and 0.0482 for all 2752 data
REM 235 parameters refined using 7 restraints
END
WGHT 0.0367 0.0639
REM Highest difference peak 0.141, deepest hole -0.175, 1-sigma level 0.039
Q1 1 0.9711 -0.6985 -0.4401 11.00000 0.05 0.14
Q2 1 0.2576 0.2547 -0.1222 11.00000 0.05 0.14
Q3 1 -0.0318 0.2392 0.0159 11.00000 0.05 0.14
Q4 1 0.8857 -0.7768 -0.5054 11.00000 0.05 0.13
Q5 1 0.7837 -0.6390 -0.1850 11.00000 0.05 0.13
Q6 1 -0.0664 -0.2375 -0.1478 11.00000 0.05 0.12
Q7 1 1.0223 -0.5849 -0.4870 11.00000 0.05 0.12
Q8 1 0.2590 -0.9497 -0.0356 11.00000 0.05 0.12
Q9 1 0.8959 -0.4324 -0.3465 11.00000 0.05 0.12
Q10 1 -0.0843 0.1378 0.0277 11.00000 0.05 0.12
Q11 1 0.2452 -0.5321 0.0373 11.00000 0.05 0.12
Q12 1 0.0113 0.4365 -0.0414 11.00000 0.05 0.12
Q13 1 0.9655 -0.3808 -0.3501 11.00000 0.05 0.12
Q14 1 0.0302 -0.0698 -0.2994 11.00000 0.05 0.11
Q15 1 0.8504 -0.3662 -0.1634 11.00000 0.05 0.11
Q16 1 0.9570 -0.7985 -0.2542 11.00000 0.05 0.11
Q17 1 0.8030 -0.7046 -0.3857 11.00000 0.05 0.11
Q18 1 -0.0476 -0.1131 -0.3733 11.00000 0.05 0.11
Q19 1 0.6667 -0.6957 -0.3267 11.00000 0.05 0.11
Q20 1 0.9574 -0.2365 -0.3860 11.00000 0.05 0.11
;
_shelx_res_checksum 51722
_olex2_submission_special_instructions 'No special instructions were received'